Reaction of organotin hydrides with acid chlorides. Mechanism of aldehyde and ester formation

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DOIResolve DOI: http://doi.org/10.1021/ja00322a031
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume106
Issue10
Pages29232931; # of pages: 9
AbstractTri-n-butyltin hydride reacts with acid chloride, RCOCl, spontaneously at ambient temperatures to form n-Bu 3SnCl, RCHO, RC(O)OCH 2R, and a number of minor products. The reaction is not a radical chain process, nor are radicals involved as intermediates. The initial products are n-Bu 3SnCl and RCHO; it is not known whether these are formed in a direct reaction between n-Bu 3SnH and RCOCl or via an unstable chloroalkoxytin species, n-Bu 3SnOCHClR. The remaining products are formed by subsequent reactions of the aldehyde. Thus, the alkoxytin species, n-Bu 3SnOCH 2R, is formed from aldehyde and tin hydride. This can react further with RCOCl to form the ester RC(O)OCH 2R, with RCHO to form n-Bu 3SnOCH(R)OCH 2R, and with n-Bu 3SnH to form RCH 2OH. The aldehyde can also react with RCOCl to form the α′-chloro ester, RC(O)OCHClR.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276528
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Record identifier4afbe9f9-2819-437b-bad2-f1381e99e118
Record created2015-10-13
Record modified2016-05-09
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