Author:
Kočovský Pavel,Černý Václav
Abstract
Participation of a 19-substituent (hydroxyl, methoxyl, acetoxyl) in hypobromous acid addition to 3- and 4-cholestenes was investigated. All three 3,4-unsaturated compounds Ia-Ic yielded exclusively the cyclic ether VI as a product of 5(O)n participation. Contrasting with this behavior, the isomeric 4-cholestenes react differently depending on the substituent at C(19): Either exclusively (IIa → XI) or predominantly (IIb → XI) with 5(O)n participation or with 6(O)π,n participation (IIc → XIVc). These results are compared with those of 19-substituted 6- and 5-cholestenes III and IV.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
16 articles.
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