PALLADIUM-CATALYZED [2,3] REARRANGEMENT OF ALKYL ALLYL SULFITES TO ALKYL ALLYLSULFONATES

被引：13

作者：

TAMARU, Y ^{[1
]}

NAGAO, K ^{[1
]}

BANDO, T ^{[1
]}

YOSHIDA, Z ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM,KYOTO 606,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 06期

关键词：

D O I：

10.1021/jo00293a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acyclic and cyclic allyl sulfites undergo a [2,3] rearrangement to furnish allylsulfonates and 1-vinyl-substituted sultones, respectively, by the catalysis of (dba)3Pd2C6H6-triethyl phosphite. Unsymmetrically substituted allylic groups of acyclic allyl sulfites rearrange to provide allylsulfonates with more substituents on the allylic positions. The rearrangement of cis and trans mixtures of cyclic allyl sulfites accompanies the stereochemical isomerization of the substituents and selectively provides trans-1,2-disubstituted sultones. © 1990, American Chemical Society. All rights reserved.

引用

页码：1823 / 1829

页数：7

共 25 条

[1]

AKERMARK B, 1985, ORGANOMETALLICS, V4, P1275

[2]

AKERMARK B, 1987, J ORGANOMET CHEM, V335, P133

[3] STUDIES IN NATURE OF ALPHA,OMEGA-REARRANGEMENT [J].