Dehydrohalogenations of cis- and trans-1-bromo-2-flourocyclohexanes

Add time:08/10/2019    Source:sciencedirect.com

Reactions of both diastereomeric vicinal bromofluorocyclohexanes with sodamide, sodium methoxide, potassium tert-butoxide, and triethylamine were studied. cis-1-Bromo-2-fluorocyclohexane eliminated almost exclusively hydrogen bromide giving mainly 1-fluorocyclohexene and a small amount of 3- fluorocyclohexene. trans-1-Bromo-2-fluorocyclohexane eliminated preferentially hydrogen fluoride on treatment with sodamide. Potassium tert- butoxide eliminated hydrogen bromide and yielded 3-fluorocyclohexene and a small amount of 1,3-cyclohexadiene, whereas sodium methoxide converted trans-1-bromo-2-fluorocyclohexane to 3-fluorocyclohexene and 3-methoxycyclohexene. Possible mechanisms and stereochemistry of the preferential elimination of hydrogen fluoride are discussed and new interpretations are offered.

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