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Steroids LXXVII. A novel rearrangement in an alcohol-lead tetraacetate reaction

โœ Scribed by David Rosenthal; Constance F. Lefler; Monroe E. Wall

Book ID
104240481
Publisher
Elsevier Science
Year
1965
Tongue
French
Weight
182 KB
Volume
6
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

the first observation of a 1,2 migration of an alkyl group from carbon to oxygen during the course of a lead tetraacetatealcohol oxidation. Previous oxidations of this type have yielded either cyclic ethers' which are formed by the attack of the activated hydroxyl group on proximate carbon atoms or by cleavage of the bond adjacent to the C-OR bond resulting in the formation of carbonyl compounds.= When 6B-methyl-B-nor-androstane-3B,58,17B-trio1,3,17-diacetate *4 (I, m.p. 90-92'; [cz]: +45'; n.m.r.: 54 c.p.s. (C-19); 6.0 g.) was heated

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