Synthesis and configurations of O-substituted hydroximoyl chlorides. Stereochemistry and mechanism of alkoxide ion substitution at the carbon-nitrogen double bond

JE Johnson, A Ghafouripour, YK Haug…

Index: Johnson, James E.; Ghafouripour, Abdolkarim; Kunz Haug, Yvonne; Cordes, A. Wallace; Pennington, William T.; Exner, Otto Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 993 - 997

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Citation Number: 31

Abstract

An X-ray crystallographic analysis of (E)-0-methyl-p-nitrobenzohydroximoyl chloride (2b) has been carried out to confirm the configuration of the compound. The dihedral angle between the benzene ring in 2b and the hydroximoyl chloride functional group is 50'. This is considerably larger than the dihedral angle between the same two planes in the (2)- hydroximoyl chloride (lb) and the 2 and E isomers of ethyl benzohydroximate (lg and 2g). ...