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.ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Carboximidate" title="Special:EditPage/Carboximidate">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Carboximidate%22">"Carboximidate"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Carboximidate%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Carboximidate%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Carboximidate%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Carboximidate%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Carboximidate%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">August 2022</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Imidate-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Imidate-2D-skeletal.png/160px-Imidate-2D-skeletal.png" decoding="async" width="160" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Imidate-2D-skeletal.png/240px-Imidate-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Imidate-2D-skeletal.png/320px-Imidate-2D-skeletal.png 2x" data-file-width="1100" data-file-height="849" /></a><figcaption>The carboximidate group</figcaption></figure> <p><b>Carboximidates</b> (or more general <b>imidates</b>) are organic compounds, which can be thought of as <a href="/wiki/Ester" title="Ester">esters</a> formed between a <a href="/wiki/Imidic_acid" title="Imidic acid">imidic acid</a> (R-C(=NR')OH) and an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, with the general formula R-C(=NR')OR". </p><p>They are also known as <b>imino ethers</b>, since they resemble <a href="/wiki/Imine" title="Imine">imines</a> (>C=N-) with an oxygen atom connected to the carbon atom of the C=N double bond.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Imidates may be generated by a number of synthetic routes,<sup id="cite_ref-rev_2-0" class="reference"><a href="#cite_note-rev-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> but are in general formed by the <a href="/wiki/Pinner_reaction" title="Pinner reaction">Pinner reaction</a>. This proceeds via the acid catalyzed attack of nitriles by alcohols. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg/500px-Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg.png" decoding="async" width="500" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg/750px-Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg/1000px-Pinner_Reaktion_Grundmecha_Version_1-Seite001.svg.png 2x" data-file-width="753" data-file-height="175" /></a><figcaption>General mechanism of the Pinner reaction<sup id="cite_ref-Mundy_156_3-0" class="reference"><a href="#cite_note-Mundy_156-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Imidates produced in this manner are formed as their hydrochloride salts, which are sometimes referred to as Pinner salts. Carboximidates are also formed as intermediates in the <a href="/wiki/Mumm_rearrangement" title="Mumm rearrangement">Mumm rearrangement</a> and the <a href="/wiki/Overman_rearrangement" title="Overman rearrangement">Overman rearrangement</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Imidate/amidate_anions"><span id="Imidate.2Famidate_anions"></span>Imidate/amidate anions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=2" title="Edit section: Imidate/amidate anions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An <b>amidate/imidate</b> anion is formed upon <a href="/wiki/Deprotonation" title="Deprotonation">deprotonation</a> of an <a href="/wiki/Amide" title="Amide">amide</a> or <a href="/wiki/Imidic_acid" title="Imidic acid">imidic acid</a>. Since amides and imidic acids are <a href="/wiki/Tautomers" class="mw-redirect" title="Tautomers">tautomers</a>, they form the same anion upon deprotonation. The two names are thus synonyms describing the same anion, although arguably, imidate refers to the resonance contributor on the left, while amidate refers to the resonance contributor on the right. However, they are distinguished when they act as ligands for transition metals, with <i>O-</i>bound species referred to as imidates and <i>N</i>-bound species referred to as amidates. They can be considered aza-substituted analogues of <a href="/wiki/Enolate" title="Enolate">enolates</a> with the formula R-N=C(O<sup>−</sup>)R. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Amidate-resonance-2D-skeletal.png" class="mw-file-description" title="Imidate/amidate resonance"><img alt="Imidate/amidate resonance" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Amidate-resonance-2D-skeletal.png/180px-Amidate-resonance-2D-skeletal.png" decoding="async" width="180" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Amidate-resonance-2D-skeletal.png/270px-Amidate-resonance-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Amidate-resonance-2D-skeletal.png/360px-Amidate-resonance-2D-skeletal.png 2x" data-file-width="1100" data-file-height="425" /></a><figcaption>Imidate/amidate resonance</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboximidates are good <a href="/wiki/Electrophiles" class="mw-redirect" title="Electrophiles">electrophiles</a> and undergo a range of addition reactions; with <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> imidates generally reacting faster than <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> imidates.<sup id="cite_ref-rev_2-1" class="reference"><a href="#cite_note-rev-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They can be <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> to give <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a> and by an analogous process react with amines (including ammonia) to form <a href="/wiki/Amidine" title="Amidine">amidines</a>. Aliphatic imidates react with an excess of alcohol under acid catalysis to form <a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">orthoesters</a> RC(OR)<sub>3</sub>, aromatic imidates can also be converted but far less readily. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Pinner_%C3%9Cbersicht_Version_2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Pinner_%C3%9Cbersicht_Version_2.svg/200px-Pinner_%C3%9Cbersicht_Version_2.svg.png" decoding="async" width="200" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Pinner_%C3%9Cbersicht_Version_2.svg/300px-Pinner_%C3%9Cbersicht_Version_2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Pinner_%C3%9Cbersicht_Version_2.svg/400px-Pinner_%C3%9Cbersicht_Version_2.svg.png 2x" data-file-width="578" data-file-height="683" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Chapman_rearrangement">Chapman rearrangement</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=4" title="Edit section: Chapman rearrangement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <b>Chapman rearrangement</b> is the thermal conversion of aryl <i>N</i>-arylbenzimidates to the corresponding amides, via intramolecular migration of an aryl group from oxygen to nitrogen.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is named after <a href="/w/index.php?title=Arthur_William_Chapman&action=edit&redlink=1" class="new" title="Arthur William Chapman (page does not exist)">Arthur William Chapman</a>, who first described it,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and is conceptually similar to the <a href="/wiki/Newman%E2%80%93Kwart_rearrangement" title="Newman–Kwart rearrangement">Newman–Kwart rearrangement</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Chapman_rearrangement.svg" class="mw-file-description" title="Chapman Rearrangement"><img alt="Chapman Rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Chapman_rearrangement.svg/300px-Chapman_rearrangement.svg.png" decoding="async" width="300" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Chapman_rearrangement.svg/450px-Chapman_rearrangement.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Chapman_rearrangement.svg/600px-Chapman_rearrangement.svg.png 2x" data-file-width="448" data-file-height="166" /></a><figcaption>Chapman Rearrangement</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="As_a_protecting_group">As a protecting group</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=5" title="Edit section: As a protecting group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Benzyl_2,2,2-trichloroacetimidate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Benzyl_2%2C2%2C2-trichloroacetimidate.svg/120px-Benzyl_2%2C2%2C2-trichloroacetimidate.svg.png" decoding="async" width="120" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Benzyl_2%2C2%2C2-trichloroacetimidate.svg/180px-Benzyl_2%2C2%2C2-trichloroacetimidate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Benzyl_2%2C2%2C2-trichloroacetimidate.svg/240px-Benzyl_2%2C2%2C2-trichloroacetimidate.svg.png 2x" data-file-width="165" data-file-height="131" /></a><figcaption>Benzyl trichloroethanimidate</figcaption></figure> <p>Carboximidates can act as <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a> for alcohols.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> For example, the base catalyzed reaction of <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">benzyl alcohol</a> upon <a href="/wiki/Trichloroacetonitrile" title="Trichloroacetonitrile">trichloroacetonitrile</a> yields a <a href="/w/index.php?title=Trichloroacetimidate&action=edit&redlink=1" class="new" title="Trichloroacetimidate (page does not exist)">trichloroacetimidate</a>. This species has orthogonal stability to acetate and <a href="/wiki/Tert-butyldimethylsilyl" class="mw-redirect" title="Tert-butyldimethylsilyl">TBS</a> protections and may be cleaved by acid hydrolysis.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Amidines" class="mw-redirect" title="Amidines">Amidines</a></li> <li><a href="/wiki/Ester" title="Ester">Esters</a></li> <li><a href="/wiki/Imidoyl_chloride" title="Imidoyl chloride">Imidoyl chloride</a> — the "acyl chloride" variant</li> <li><a href="/wiki/Oxazoline" title="Oxazoline">Oxazoline</a> — the corresponding 5-membered heterocycle</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carboximidate&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/pinner-reaction.shtm">"Pinner Reaction"</a>. <i>Organic Chemistry Portal</i>. Buckten, CH: Reto Mueller<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-09-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Organic+Chemistry+Portal&rft.atitle=Pinner+Reaction&rft_id=https%3A%2F%2Fwww.organic-chemistry.org%2Fnamedreactions%2Fpinner-reaction.shtm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> <li id="cite_note-rev-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-rev_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-rev_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRogerNeilson,_Douglas_G.1961" class="citation journal cs1">Roger, Robert; Neilson, Douglas G. (1961). "The Chemistry of Imidates". <i><a href="/wiki/Chemical_Reviews" title="Chemical Reviews">Chemical Reviews</a></i>. <b>61</b> (2): 179–211. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60210a003">10.1021/cr60210a003</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=The+Chemistry+of+Imidates.&rft.volume=61&rft.issue=2&rft.pages=179-211&rft.date=1961&rft_id=info%3Adoi%2F10.1021%2Fcr60210a003&rft.aulast=Roger&rft.aufirst=Robert&rft.au=Neilson%2C+Douglas+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> <li id="cite_note-Mundy_156-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Mundy_156_3-0">^</a></b></span> <span class="reference-text">B. P. Mundy, M. G. Ellerd, F. G. Favaloro: <i>Name Reactions and Reagents in organic Synthesis</i>, 2. Auflage, Wiley-Interscience, Hoboken, NJ <b>2005</b>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-22854-7" title="Special:BookSources/978-0-471-22854-7">978-0-471-22854-7</a>, S. 516.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchulenberg,_J._W.Archer,_S.1965" class="citation journal cs1">Schulenberg, J. W.; Archer, S. (1965). "The Chapman Rearrangement". <i><a href="/wiki/Organic_Reactions" title="Organic Reactions">Organic Reactions</a></i>. <b>14</b>: 1–51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471264180.or014.01">10.1002/0471264180.or014.01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0471264180" title="Special:BookSources/0471264180"><bdi>0471264180</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Reactions&rft.atitle=The+Chapman+Rearrangement&rft.volume=14&rft.pages=1-51&rft.date=1965&rft_id=info%3Adoi%2F10.1002%2F0471264180.or014.01&rft.isbn=0471264180&rft.au=Schulenberg%2C+J.+W.&rft.au=Archer%2C+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChapman1925" class="citation journal cs1">Chapman, Arthur William (1925). "CCLXIX.—Imino-aryl ethers. Part III. The molecular rearrangement of <i>N</i>-phenylbenziminophenyl ether". <i>J. Chem. Soc., Trans</i>. <b>127</b>: 1992–1998. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FCT9252701992">10.1039/CT9252701992</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.%2C+Trans.&rft.atitle=CCLXIX.%E2%80%94Imino-aryl+ethers.+Part+III.+The+molecular+rearrangement+of+N-phenylbenziminophenyl+ether&rft.volume=127&rft.pages=1992-1998&rft.date=1925&rft_id=info%3Adoi%2F10.1039%2FCT9252701992&rft.aulast=Chapman&rft.aufirst=Arthur+William&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWutsGreene,_Theodora_W.2006" class="citation book cs1">Wuts, Peter G. M.; Greene, Theodora W. (2006). <i>Protective groups in organic synthesis</i> (4th ed.). Hoboken, N.J.: WILEY. p. 244. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-69754-1" title="Special:BookSources/978-0-471-69754-1"><bdi>978-0-471-69754-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Protective+groups+in+organic+synthesis.&rft.place=Hoboken%2C+N.J.&rft.pages=244&rft.edition=4th&rft.pub=WILEY&rft.date=2006&rft.isbn=978-0-471-69754-1&rft.aulast=Wuts&rft.aufirst=Peter+G.+M.&rft.au=Greene%2C+Theodora+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYuYu,_HaiHui,_YongzhengHan,_Xiuwen1999" class="citation journal cs1">Yu, Biao; Yu, Hai; Hui, Yongzheng; Han, Xiuwen (June 1999). "Trichloroacetimidate as an Efficient Protective Group for Alcohols". <i>Synlett</i>. <b>1999</b> (6): 753–755. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-1999-2736">10.1055/s-1999-2736</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synlett&rft.atitle=Trichloroacetimidate+as+an+Efficient+Protective+Group+for+Alcohols&rft.volume=1999&rft.issue=6&rft.pages=753-755&rft.date=1999-06&rft_id=info%3Adoi%2F10.1055%2Fs-1999-2736&rft.aulast=Yu&rft.aufirst=Biao&rft.au=Yu%2C+Hai&rft.au=Hui%2C+Yongzheng&rft.au=Han%2C+Xiuwen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarboximidate" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Carboximidate&oldid=1243741076">https://en.wikipedia.org/w/index.php?title=Carboximidate&oldid=1243741076</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Carboximidates" title="Category:Carboximidates">Carboximidates</a></li><li><a href="/wiki/Category:Functional_groups" title="Category:Functional groups">Functional groups</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_needing_additional_references_from_August_2022" title="Category:Articles needing additional references from August 2022">Articles needing additional references from August 2022</a></li><li><a href="/wiki/Category:All_articles_needing_additional_references" title="Category:All articles needing additional references">All articles needing additional references</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 3 September 2024, at 04:43<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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