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Reaction of Organic Selenocyanates with Hydroxides: The One‐Pot Synthesis of Dialkyl Diselenides from Alkyl Bromides
Author(s) -
Krief Alain,
Dumont Willy,
Delmotte Cathy
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000502)39:9<1669::aid-anie1669>3.0.co;2-6
Subject(s) - chemistry , aryl , hydroxide , alkyl , tetrabutylammonium hydroxide , organic chemistry , molar ratio , catalysis
The amount of hydroxide used in the reaction with organic selenocyanate determines the identity of the product (see scheme). Dialkyl and diaryl diselenides are efficiently prepared with 0.5 equivalents of hydroxide, whereas the reaction of aryl selenocyanates with at least one molar equivalent of hydroxide leads to the formation of aryl selenolates. R = Ph, Bu, i Pr, PhCH 2 ; M = Li, Na, K.