Tetrahedron

N-nitrosothialdine. Synthesis, X-ray crystallography, and NN rotational barrier

TJ Hansen, RM Angeles, LK Keefer, CS Day…

Index: Hansen, Thomsen J.; Angeles, Rosalie M.; Keefer, Larry K.; Day, Cynthia S.; Gaffield, William Tetrahedron, 1981 , vol. 37, # 27 p. 4143 - 4149

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Citation Number: 17

Abstract

Crystalline N-nitrosothialdine (2) has been prepared in 38% yield by treating thialdine (1) with n-butyl nitrite and acetic acid in hexane. X-Ray crystallography of 2 revealed that its three methyl groups are a11 cis and, rather surprisingly, all equatorial; this finding contrasts sharply with results for other nitrosamine heterocycles which have been investigated, whose bulky alpha substituents are forced into a primarily axial orientation by the large steric ...