Abstract
The participation propensity, in hypobromous acid addition, of various ambident neighbouring groups containing a carbonyl moiety has been studied for steroidal olefins (1)–(3). The carbamoyloxy group (–OCONH2) has been found to be superior to other groups. The relative importance of the electronic (Markownikoff) and stereoelectronic effects in electrophilic additions has also been elucidated. In cases where these effects are dissonant, the neighbouring group participation may alter the regioselectivity of the reaction. A new method of synthesis of unsubstituted carbamates has been developed.
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