Some observations on the chemical and electrochemical reductions of 8-Bromobornan-2-one

Abstract

Reduction of 8-bromobornan-2-one (1) by sodium-potassium alloy in ether, or hexane, gives p-menth-8-en-2-one (3) but in hexamethylphosphoric triamide the product is bornan-2-one (2). Electrochemical reductions at mercury cathodes both in dimethylformamide and hexamethyl-phosphoric triamide give mostly compound (3). Reduction of bromide (1) by tributylstannane is concentration dependent. In concentrated solution compound (2) is the major product but in more dilute solutions compound (3) becomes predominant.