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1,2-cyanoselenenylation of olefins. Reaction of enamines with phenyl selenocyanate

✍ Scribed by Shuji Tomoda; Yoshito Takeuchi; Yujiro Nomura

Book ID: 104220604
Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 256 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87105-1

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✦ Synopsis

The first 1,2-cyanoselenenylatlon of carbon-carbon double bond has been achieved by the reaction of SIX enamlnes derived from ketones or aldehydes with phenyl selenocyanate in ethanol. The products, 2-phenylseleno-1-amlnocarbonltrlles, were obtalned In al-98% yield with complete reglo-and stereospeclflclty.

Among many useful synthetic reactions involving organoselenlum reagents2, 1,2-addition across carbon-carbon double bonds is an extremely powerful synthetic method leadlng to the formation of various organic compounds lncludlng heterocycles.

3-10 Nucleophlles used In this methodology have been halIdes? hydroxide4, alkoxlde 5 , carboxyl 5,6 , urethane',

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