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Communication | Regular issue | Vol 22, No. 9, 1984, pp.1955-1958
Published online, 1st January, 1970
DOI: 10.3987/R-1984-09-1955
A Novel Ring-opening Reaction of Aziridine Induced by the Formation of Nitrogen-substituted Carbanion of Nonstabilized Type

Otohiko Tsuge,* Shuji Kanemasa, Hiroyuki Suga, and Koyo Matsuda

*Graduate School of Engineering, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan


Desilylation of 1-(trimethylsilylmethyl)aziridines causes a novel ring-opening reaction of aziridine. Only aziridines whose ring bears at least one anion-stabilizing moiety undergo the desilylation, and the resultant carbanion of nonstabilized type changes into a stabilized one inviting the ring-opening. The types of products depend upon the number of anion-stabilizing moieties as well as the quenching reagents employed.