Reactions of aryldiazomethanes with chloranil.

T Oshima, T Nagai

Index: Oshima, Takumi; Nagai, Toshikazu Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 3 p. 726 - 730

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Citation Number: 13

Abstract

The reactions of several aryldiazomethanes (1a: p-tolyl; 1b: phenyl; 1c: p-chlorophenyl) with chloranil gave stilbenes (3) and spiro-oxetanes (4) at 20° C in tetrahydrofuran or 1, 2- dichloroethane. The isomer ratios of 3 were ca. 2 to 3: 1 in favor of cis, depending on the solvents and on the substituents of 1. In the case of 4, however, stable trans-isomers were selectively formed. On the other hand, the presence of added CH 3 OH suppressed the ...