The Journal of Organic Chemistry

Cyclopropylcarbinyl radical reactions in the cycloprop [2.3] indene system

EC Friedrich, RL Holmstead

Index: Friedrich,E.C.; Holmstead,R.L. Journal of Organic Chemistry, 1971 , vol. 36, # 7 p. 971 - 975

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Citation Number: 25

Abstract

6a HH 6b 4 em-and endo-1-bromocycloprop [2, 3] indenes (2 and 3) are formed via the cyclopropylcarbinyl radical intermediate 6a, resulting from initial abstraction of a hydrogen atom from the 1 position of cycloprop [2, 3] indene. 1-Bromomethylindene (4) results via bromine attack on the rearranged allylcarbinyl radical 6b. Finally, a probable pathway for the formation of naphthalene is via reaction of the allylcarbinyl radical 6c with bromine to give ...

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