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Note | Regular issue | Vol 55, No. 12, 2001, pp.2387-2395
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9327
Synthesis of 6-Bromo-4-methylbenzofuroxan

Tohru Takabatake,* Aki Takei, Tomoyuki Miyazawa, Minoru Hasegawa, and Shinichi Miyairi

*College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba
274-8555, Japan

Abstract

6-Bromo-4-methylbenzofuroxan (3) was prepared by the thermal decomposition of 4-bromo-2-methyl-6-nitrophenylazide in excellent yields. 1H-NMR spectra showed that the compound (3) rapidly rearranges between the two unsymmetrical bicyclic structures. However, the methyl group and bromine may possibly function as a barrier against molecular rearrangement and so molecular rearrangement is slow enough that different chemical shifts are apparent at room temperature.