Unimolecular chain transfer (UMCT) reactions: Concepts, preliminary results with silicon hydrides, and future potential

被引：45

作者：

Curran, DP

Xu, JY

Lazzarini, E

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 24期

关键词：

D O I：

10.1039/p19950003049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Most radical reactions are conducted by chain methods that have bimolecular chain transfer steps. It is proposed that unimolecular chain transfer (UMCT) reactions should have advantages for conducting difficult radical transformations. The concepts of the UMCT method are illustrated with allyltributylstannane, and the first examples of UMCT reactions of silicon hydrides are introduced. Examples of bimolecular reactions conducted with silicon hydride UMCT reagents are provided, and the potential of the UMCT method is discussed.

引用

页码：3049 / 3059

页数：11

共 44 条

[1] SYNTHESIS OF GAMMA-HALOESTERS AND GAMMA-KETOESTERS BY HOMOLYTIC ADDITION OF CARBON RADICALS GENERATED BY ALPHA-HALOESTERS AND TRIETHYLBORANE TO ALKENES AND SILYL ENOL ETHERS
BACIOCCHI, E
MURAGLIA, E
[J]. TETRAHEDRON LETTERS, 1994, 35 (17) : 2763 - 2766
[2] TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS
BALLESTRI, M
CHATGILIALOGLU, C
CLARK, KB
GRILLER, D
GIESE, B
KOPPING, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 678 - 683
[3] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS WITH LOW HYDROGEN DONATING ABILITIES
BALLESTRI, M
CHATGILIALOGLU, C
GUERRA, M
GUERRINI, A
LUCARINI, M
SECONI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03): : 421 - 425
[4] THE INVENTION OF RADICAL REACTIONS .29. RADICAL MONODEOXYGENATIONS AND DIDEOXYGENATIONS WITH SILANES
BARTON, DHR
JANG, DO
JASZBERENYI, JC
[J]. TETRAHEDRON, 1993, 49 (14) : 2793 - 2804
[5] TRIS(TRIMETHYLSILYL)SILANE AND DIPHENYLSILANE IN THE RADICAL CHAIN DIDEOXYGENATION OF 1,6-ANHYDRO-D-GLUCOSE - A COMPARATIVE-STUDY
BARTON, DHR
JANG, DO
JASZBERENYI, JC
[J]. TETRAHEDRON LETTERS, 1992, 33 (44) : 6629 - 6632
[6] RADICAL MONODEOXYGENATION AND DIDEOXYGENATION WITH THE TRIETHYLSILANE + BENZOYL PEROXIDE SYSTEM
BARTON, DHR
JANG, DO
JASZBERENYI, JC
[J]. TETRAHEDRON LETTERS, 1991, 32 (49) : 7187 - 7190
[7] THE INVENTION OF RADICAL REACTIONS .31. DIPHENYLSILANE - A REAGENT FOR DEOXYGENATION OF ALCOHOLS VIA THEIR THIOCARBONYL DERIVATIVES, DEAMINATION VIA ISONITRILES, AND DEHALOGENATION OF BROMO-COMPOUNDS AND IODO-COMPOUNDS BY RADICAL-CHAIN CHEMISTRY
BARTON, DHR
JANG, DO
JASZBERENYI, JC
[J]. TETRAHEDRON, 1993, 49 (33) : 7193 - 7214
[8] ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2121 - 2128
[9] A COMMENT ON THE USE OF TRIETHYLSILANE AS A RADICAL-BASED REDUCING AGENT
CHATGILIALOGLU, C
FERRERI, C
LUCARINI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) : 249 - 251
[10] CHATGILIALOGLU C, 1989, FREE RADICALS SYNTHE, P215

← 1 2 3 4 5 →