On the mechanism of the Shapiro reaction: Understanding the regioselectivity
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Universidad de La Rioja
info
ISSN: 2046-2069
Any de publicació: 2015
Volum: 5
Número: 47
Pàgines: 37292-37297
Tipus: Article
Altres publicacions en: RSC Advances
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Resum
A detailed DFT-level mechanism elucidation of the two-step reaction of tosylhydrazones with alkyllithium reagents (the Shapiro reaction) is presented. A rationale of the experimental regioselectivity is offered together with some suggestions for modifying the experimental main regioisomer. Also, the proposed general mechanism was checked with a recent modification of the Shapiro reaction involving a fluorination reaction. © 2015 The Royal Society of Chemistry.