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The reaction of 1-methyltricyclo [4.4.0.02,6decaN-3-one and related compounds with hydrogen bromide in acetic acid

✍ Scribed by Drury Caine; Anibal A. Boucugnani; Chia-Yeh Chu; Samuel L. Graham; Troy L. Smith Jr.

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
260 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

In recent years there has been considerable interest in the mode of cleavage of conjugated cyclopropyl ketones with electrophilic reagents. 2 l-Methyltricyclol4.4.0.0 2'6]decan-3-one(&,) and derivatives which have both 8 carbons of the cyclopropane ring fully substituted in principle can give Spiro or fused-ring halo ketones upon reaction with electrophilic reagents such as halogen acids. However, ketones 4 and 5 which have a tricyclo[4.4.0.0 2'6]d ecan-2-one moiety fused to the C ring of a steroid system have been found to yield only fused-ring products z3 and k4 upon reaction with hydrogen chloride or hydrogen bromide in acetic acid.

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