Preparation of dl-Dibenzophenanthrene by Using Benzyl-type Binaphthyl Disulfone

Abstract

Abstract: We reported that a benzyl-type binaphthyl disulfone could be conveniently converted into dibenzophenanthrene. Thus, racemic 1 was treated with lithium diisopropylamide (LDA) afforded dl-dibenzophenanthrene in a moderate yield, together with an unknown benzensulfonyl-substituted derivative 2. The structures were confirmed by MS, ¹H, ¹³CNMR and elemental analysis. The reaction might involve the initiaLIntramolecular nucleophilic substitution to produce an intermediate 3, followed by elimination of benzenesulfinic acid to form dibenzophenanthrene.

Key words: Binaphthyl disulfone, Dibenzophenanthrene, Reaction mechanism, Intramolecular nucleophilic substitution, Elimination=

CLC Number:

O624

TrendMD:

AN De-Lie, TAN Xiao-Hua, PENG Zhi-Hong, SHAO Guang . Preparation of dl-Dibenzophenanthrene by Using Benzyl-type Binaphthyl Disulfone[J]. Chem. J. Chinese Universities, 2003, 24(12): 2218.

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Preparation of dl-Dibenzophenanthrene by Using Benzyl-type Binaphthyl Disulfone

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