Tetrahedron p. 4143 - 4149 (1981)
Update date:2022-09-26
Topics:
Hansen, Thomsen J.
Angeles, Rosalie M.
Keefer, Larry K.
Day, Cynthia S.
Gaffield, William
Crystalline N-nitrosothialdine (2) has been prepared in 38percent 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 all 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 requirement of the N-N-O system.The equatorial methyl group both displaces the nitroso group from the C-N-C plane and twists it somewhat about the N-N bond.N-Nitrosothialdine's unusually low barrier to rotation about the N-N bond (72 kJ/mole) is attributed to this steric crowding, combined with inductive electron withdrawal by the two sulfur atoms.
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Doi:10.1021/om049352v
(2004)Doi:10.3184/030823407X198177
(2007)Doi:10.1021/jo00139a023
(1982)Doi:10.1080/00397919708003381
(1997)Doi:10.1021/ja0401702
(2004)Doi:10.1016/S0040-4039(00)87009-4
(1982)