Participation of 19-substituents in electrophilic additions. influence of 3β-substitution on hypobromous acid addition to 5,6-unsaturated steroids
1980 ◽
Vol 45
(11)
◽
pp. 3023-3029
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Reactions of 19-hydroxy-, methoxy- and acetoxy-5-cholestenes Ia, IIa, IIIa were studied and compared with those previously obtained with analogous 3β-acetoxy-19-substituted 5-cholestenes Ib, IIb, IIIc. A marked difference was found in 19-acetoxy derivatives where the 3-unsubstituted compound IIIa yields exclusively the bromohydrin XVIa as a product of 6(O)π,n participation while the 3β-acetoxy derivative IIIb gives, apart from the analogous bromohydrin XVIb, also products of competing reactions: The epoxide XIIb and the bromohydrin XIIIb.
1983 ◽
Vol 48
(12)
◽
pp. 3618-3628
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1988 ◽
pp. 2297-2303
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1983 ◽
Vol 48
(10)
◽
pp. 2994-3019
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Keyword(s):
1983 ◽
Vol 48
(12)
◽
pp. 3660-3673
◽
1982 ◽
Vol 47
(11)
◽
pp. 3062-3076
◽
1987 ◽
pp. 1969-1974
◽
1981 ◽
Vol 22
(28)
◽
pp. 2699-2702
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Keyword(s):