1-(N-TRIMETHYLSILYL-S-PHENYLSULFONIMIDOYL)-3-METHYL-2-BUTENYL LITHIUM-2(12-CROWN-4) - STRUCTURE OF A LITHIATED ALLYLIC SULFOXIMINE IN THE CRYSTAL AND COMPARISON WITH MODEL AB-INITIO CALCULATIONS

被引：32
作者：
GAIS, HJ
LENZ, D
RAABE, G
机构：
[1] Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule Aachen, 52056 Aachen
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期
关键词：
D O I：
10.1016/0040-4039(95)01555-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The crystal structures of the lithiated allylic sulfoximine 1a(12-c-4)(2), which is a solvent separated contact ion pair, and of the allylic sulfoximine 3b were determined. The anion of 1a(12-c-4)(2), adopts a conformation in which the lone pair orbital at the C-alpha-atom is gauche to the O- and the N-atom. The C-alpha-S bond is considerably shortened. Similar to alpha-sulfonyl carbanions the conformation of alpha-sulfonimidoyl carbanions seems to be determined by negative hyperconjugation. Ab initio calculations (6-31+G*) of various conformers of the anion 4 (a-c) suggest a low configurational stability of the C-alpha-atom of 1.
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页码：7437 / 7440
页数：4
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