The Journal of Organic Chemistry

Nitrations with Acetyl Nitrate. III. Nitration with 1, 1-Diarylalkenes1

FG Bordwell, EW Garbisch Jr

Index: Bordwell,F.G.; Garbisch,E.W. Journal of Organic Chemistry, 1962 , vol. 27, p. 3049 - 3055

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Citation Number: 26

Abstract

Nitrations of 1, l-diarylalkenes with acetyl nitrate generally were found to give p-nitro acetates as the principal products (17-90%). However, in the absence of sulfuric acid catalyst, nitroalkenes or@-nitro nitrates were sometimes found to predominate. The formation of p-nitro acetates from cis-or trans-1-p-chlorophenyl-1-phenylpropenes was found to be nonstereospecific. This observation and the ready exchange of the acetoxy ...