Journal of Organic Chemistry p. 4331 - 4339 (1981)
Update date:2022-08-04
Topics:
VanCantfort, Christopher K.
Coates, Robert M.
Metalation of chrysanthemic nitrile 1 with lithium diisopropylamide followed by sulfenylation with diphenyl disulfide or oxygenation with a molybdenum peroxide complex gave chrysanthemic nitrile derivatives bearing phenylthio (3 and 4) or hydroxyl (6) substituents at C-1.These compounds provided access to the following series of 1-substituted chrysanthemylamines: 1-(phenylthio)chrysanthemylamine (5), 1-methoxychrysanthemylamine (8), 1-methoxydihydrochrysanthemylamine (10), and the N-nitrosooxazolidinone (13) derived from 1-hydroxychrysanthemylamine (11).Nitrous acid deamination of 5 and 8 and hydrolytic deamination of 13 gave acyclic alcohols (14, 17, and 18) related in structure to yomogi alcohol as major products by cleavage of the 1-3 cyclopropane ring bond.Products formed by cleavage of the 1-2 cyclopropane ring bond (15 and 24) and related in structure to santolinatriene were obtained in lesser amounts from the deamination of 5 and 13.Pinacol-type ring expansion to the isomeric cyclobutanones 19 and 20 was observed as a minor reaction pathway in the deaminations of 8 and 13.In contrast, deamination of 10 gave dihydrocyclobutanones 21 and 22 as the major isolated products.
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