Selection of a Sommelet-Hauser or a Stevens rearrangement pathway of N, N-dimethyl (substituted benzyl) ammonium N-alkylides

T Tanaka, N Shirai, J Sugimori…

Index: Tanaka, Tetsuya; Shirai, Naohiro; Sugimori, Junji; Sato, Yoshiro Journal of Organic Chemistry, 1992 , vol. 57, # 18 p. 5034 - 5036

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Citation Number: 32

Abstract

Table 111, the product changed to NJV-dimethyl-5-methoxy-2-methylbenzylamine (4c) in the presence of DBU (entry 2) and changed to NJV-dimethyl-2-(4-methoxy-pheny1) ethylamine (Sc) under irradiation with a 100-W medium-pressure mercury lamp (entry 3). In the reaction of a 4methylbenzyla" onium ealt (le), the ratio of 48 to Se in HMPA was reversed under W irradiation at 10 OC, but a mixture of both products was formed at room ...