The Journal of Organic Chemistry

Regioselective route to sterically hindered cyclopropylcarbinyl halides

RT Hrubiec, MB Smith

Index: Hrubiec, Robert T.; Smith, Michael B. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 431 - 435

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Citation Number: 45

Abstract

Reaction of cyclopropylcarbinyl alcohols 1 with hexachloroacetone and triphenylphosphine resulted in 8040% yields of the Corresponding cyclopropylcarbinyl chlorides 4 regioselectively, with no trace of the homoallylic chloride 2 or the chlorocyclobutane derivative 6a. Similar reaction of 1 with bromine and triphenylphosphine, in dimethylformamide, gave 6540% yields of the cyclopropylcarbinyl bromide 5 with trace ...

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