SIGNIFICANT ORBITAL INTERACTIONS IN PI-FACIAL STEREOSELECTION OF ELECTROPHILIC ADDITION-REACTIONS TO VINYLIC SULFOXIDES

被引：14

作者：

FUJITA, M

ISHIDA, M

MANAKO, K

SATO, K

OGURA, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Chiba University 1-33 Yayoicho, Inageku, Chiba

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 04期

关键词：

ELECTROPHILIC ADDITION; PI-FACIAL STEREOSELECTION; ORBITAL INTERACTIONS; VINYLIC SULFOXIDE;

D O I：

10.1016/S0040-4039(00)61642-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both theoretical and experimental studies demonstrated that the pi-facial stereoselection of the electrophilic addition reactions to vinylic sulfoxides is ascribed to a transition-state model in which the lone pair and the oxygen atom are oriented at the anti and inside positions, respectively, to the incipient bond.

引用

页码：645 / 648

页数：4

共 26 条

[21]

PRETSCH E, 1981, TABELLEN STRUCTURAUF, pH210

[22] OPTIMIZATION OF PARAMETERS FOR SEMIEMPIRICAL METHODS .2. APPLICATIONS [J].