Abstract
Allylic halogenation of t-butylcyclohexene (2a) with t-butyl hypochlorite or
N-bromosuccinimide affords mixtures containing mainly trans-5-t-butyl-3-chlorocyclohexene (2b) and the corresponding trans bromo compound (2c) respectively.
The copper-catalysed reaction of (2a) with t-butyl perbenzoate
shows similar but less pronounced stereoselectivity. Halogen-atom abstraction
by tributyltin radicals, generated from tributylstannane,
proceeds more rapidly from the trans
halides (2b) and (2c) than from their cis
epimers (3b) and (3c). These results suggest that homolytic fission or formation of allylic C-halogen bonds
is sensitive to stereoelectronic effects.
Cited by
13 articles.
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