Canadian Journal of Chemistry p. 2355 - 2357 (1982)
Update date:2022-07-29
Topics:
Agami, C.
Rizk, T.
Durand, R.
Geneste, P.
The relative reactivities of a number of cis/trans pairs of bicyclic ketones in the 1- and 2-decalone series (2-decalone; 10-methyl-2-decalone; 9-methyl-1-decalone; and 3,10-dimethyl-2-decalone) have been studied for the nucleophilic addition of hydroxylamine in acidic medium.The results obtained as well as the rate constants for neutral or acid catalysed addition always reveal a slight preference for the trans-isomer (x 2.4).This result agrees with the proposal that preferential equatorial attack of a nucleophile is caused by conformational factors related to a steroid <*> non-steroid conformation equilibrium in the cis-isomers.
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