Volume 19, Issue 4
Preparative Organic Chemistry
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ChemInform Abstract: Reduction of gem-Dibromocyclopropanes with Dialkyl Phosphonate and Amine.

T. HIRAO

T. HIRAO

Dep. Appl. Chem., Fac. Eng., Osaka Univ., Suita-shi 565, Japan

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T. MASUNAGA

T. MASUNAGA

Dep. Appl. Chem., Fac. Eng., Osaka Univ., Suita-shi 565, Japan

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K. HAYASHI

K. HAYASHI

Dep. Appl. Chem., Fac. Eng., Osaka Univ., Suita-shi 565, Japan

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Y. OHSHIRO

Y. OHSHIRO

Dep. Appl. Chem., Fac. Eng., Osaka Univ., Suita-shi 565, Japan

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First published: January 26, 1988

Abstract

The dialkyl phosphonates (II) are employed in the reduction debromination of the bicyclic geminal dibromide (I) to give mixtures of the endo- and exo-bromides (III).

ChemInform Abstract

The dialkyl phosphonates (II) are employed in the reduction debromination of the bicyclic geminal dibromide (I) to give mixtures of the endo- and exo-bromides (III). The best results are obtained using diethyl phosphonate (IIb) in the presence of triethylamine. The influence of other bases is also tested. Treatment of the cyclopropyl dibromides (IV) and (VI) with (IIb)/Et3N yields the monobromides(V) or (VII).

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