
TY  - JOUR
A1  - Beckwith, ALJ 
A1  - Westwood, SW 
T1  - Reactions of cyclohexenyl halides with tributylstannane. Stereoelectronic effects on S<sub>H</sub>2 reactions at halogen
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 11
SP  - 2123
EP  - 2132
KW  - 
UR  - https://doi.org/10.1071/CH9832123 
N2  - 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. 
ER  -

