Tetrahedron Letters

Nucleophilic cleavage of 2, 2-dimethylaziridines: competition between SN2 and postulated “SET” mechanism.

H Stamm, P Assithianakis, B Buchholz, R Weiβ

Index: Stamm, H.; Assithianakis, P.; Buchholz, B.; Weiss, R. Tetrahedron Letters, 1982 , vol. 23, # 48 p. 5021 - 5024

Full Text: HTML

Citation Number: 41

Abstract

Abstract Regioselectivity of nucleophilic attack on 2, 2-dimethylaziridines depends on the degree of leaving group activation: in highly activated aziridines it occurs at the methylene carbon and in less activated at the tertiary carbon. This latter abnormal ring opening is explained by an SET mechanism.

~20%

~77%

Reductive ring opening of N-acylaziridines: Different outcom...

[Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Stamm, H.; Tardivel, R. Tetrahedron Letters, 1989 , vol. 30, # 17 p. 2271 - 2272]

Radical combination in the ortho position of trityl radical ...

[Werry, Juergen; Lin, Pen-Yuan; Bellos, Konstantinos; Assithianakis, Petros; Stamm, Helmut Journal of the Chemical Society, Chemical Communications, 1990 , # 20 p. 1389 - 1390]

Electron attachment to N-benzoylaziridines followed by C–N h...

[Stamm, Helmut; Assithianakis, Petros; Weiss, Rainer; Bentz, Gunther; Buchholz, Berthold Journal of the Chemical Society, Chemical Communications, 1984 , # 12 p. 753 - 754]