The Journal of Organic Chemistry

Stereochemistry of the reversible cyclization of. omega.-formylalkyl radicals

ALJ Beckwith, KD Raner

Index: Beckwith, A. L. J.; Raner, K. D. Journal of Organic Chemistry, 1992 , vol. 57, p. 4954 - 4962

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Citation Number: 46

Abstract

The reactions of 6-bromo-4-(l', l'dimethylethyl) hexanal (4), 5bromo-3-(l', l'-dimethylethyl) pentanal (ll), and 5-bromo-4-(l ', l'-dimethylethyl) pentanal (17) with tributylstannane have been investigated in detail. The major producta are the debrominated aldehydes and cycloalkanols which arise from the cyclization of the intermediate u-formyhlkyl radicals. The stemxhemical outcome of the cyclization of thw radicals is dependent on the etanuane ...