Inverse Neighboring Group Participation: Explanation of an Unusual S -} N Alkyl Migration of lsothiuronium Salts Containing a Lactone Group

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896102" target="_blank" >RIV/00216275:25310/13:39896102 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/13:10159277
Result on the web
<a href="http://dx.doi.org/10.1021/jo400460x" target="_blank" >http://dx.doi.org/10.1021/jo400460x</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo400460x" target="_blank" >10.1021/jo400460x</a>

Result language
angličtina
Original language name
Inverse Neighboring Group Participation: Explanation of an Unusual S -} N Alkyl Migration of lsothiuronium Salts Containing a Lactone Group
Original language description
A detailed experimental and DFT study of the S to N alkyl migration of substituted S-(1(3H)-isobenzofuranon-3-yl)isothiuronium bromide to N,N'-dimethyl-N-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thiourea provided evidence for the existence of an unusual double displacement mechanism involving two consecutive back-side S(N)2 reactions where a carboxylate anion has a crucial role both as a leaving group as well as an internal nucleophile. The thiazetidine zwitterionic species that is involved in this mechanism as an intermediate was characterized by infrared multiphoton dissociation spectroscopy and was trapped with methyl iodide. It was found that the intermediate has a structure of a free ion pair. The double-displacement mechanism can be considered as a new type of inverse lactone neighboring group participation.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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