Chloride Ion Catalyzed Conformational Inversion of Carbocation Intermediates in the Hydrolysis of a Benzo[a]pyrene 7,8-Diol 9,10-Epoxide

A highly efficient procedure for converting 7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (1) to its trans-9,10-chlorohydrin (5) with excellent yield and purity by the reaction of anhydrous HCl in THF has been developed. The rate of reaction of 5 has been determined as a function of...

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Veröffentlicht in:Journal of the American Chemical Society 2002-12, Vol.124 (48), p.14382-14387
Hauptverfasser: Doan, Lanxuan, Yagi, Haruhiko, Jerina, Donald M, Whalen, Dale L
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Sprache:eng
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