N. Kamigata, T. Kurihara, H. Minato
Nov 1, 1971
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Benzenediazonium tetrafluoroborate in dimethyl sulfoxide decomposed instantaneously with evolution of nitrogen upon addition of a dimethyl sulfoxide solution of choline or tetramethylammonium hydroxide. Orientations and partial rate factors for the phenylation of substituted benzenes indicated that the phenylating agent is not phenyl cation but phenyl radical. Hammett’s plots of partial rate factors for meta and para substitutions were good straight lines with ρm=0.34, ρp=1.63 (in choline) and ρm=0.48, ρp=1.69 (in tetramethylammonium hydroxide solutions). Decomposition of benzenediazonium tetrafluoroborate by tetramethylammonium hydroxide in aqueous solution was also studied, and the orientation and partial rate factors for the phenylation of substituted benzenes were determined.