MECHANISM OF SOLVOLYSIS OF 2-HALOGENOALKYLSILANES .I. STERIC ASPECTS

被引：78

作者：

JARVIE, AWP

HOLT, A

THOMPSON, J

机构：

[1] Chemistry Department, University of Aston in Birmingham

来源：

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC | 1969年 / 07期

关键词：

D O I：

10.1039/j29690000852

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solvolysis of erythro-1,2-dibromopropyltrimethylsilane in aqueous ethanol at room temperature has been shown to result in the highly stereospecific trans-elimination of trimethylbromosilane. A mechanism is suggested which involves initial cleavage of the carbon-halogen bond assisted by participation of the silicon with the developing positive charge on the carbon atom.

引用

页码：852 / &

共 19 条

[11] HOFFMANN HM, 1967, TETRAHEDRON LETT, P4393
[12] THE NATURE OF THE RATE-DETERMINING STEP IN DEOXYMERCURATION
KREEVOY, MM
KOWITT, FR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) : 739 - 745
[13] KUMADA M, 1968, ADV ORGANOMETALLIC C, V6, P21
[14] PREPARATION OF ORGANOLITHIUM COMPOUNDS BY TRANSMETALATION REACTION .7. CIS- + TRANS-PROPENYLLITHIUM - STEREOCHEMISTRY OF TRANSMETALATION REACTION . ISOPROPENYLLITHIUM
SEYFERTH, D
VAUGHAN, LG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) : 883 - &
[15] ORGANOSILICON COMPOUNDS .16. FURTHER STUDIES OF BETA-ELIMINATIONS INVOLVING SILICON
SOMMER, LH
BAILEY, DL
WHITMORE, FC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (09) : 2869 - 2872
[16] ORGANOSILICON COMPOUNDS .5. BETA-ELIMINATIONS INVOLVING SILICON
SOMMER, LH
GOLDBERG, GM
DORFMAN, E
WHITMORE, FC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (06) : 1083 - 1085
[17] SILICONIUM IONS AND CARBONIUM IONS AS REACTION INTERMEDIATES
SOMMER, LH
BAUGHMAN, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (15) : 3346 - &
[18] THE REACTIVITY WITH ALKALI OF CHLORINE CARBON BOND-ALPHA, BOND-BETA AND BOND-GAMMA TO SILICON
SOMMER, LH
DORFMAN, E
GOLDBERG, GM
WHITMORE, FC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (03) : 488 - 489
[19] SOMMERLH, 1965, STEREOCHEMISTRY MECH, P144

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