PROGRESS OF THE BARTON-MCCOMBIE METHODOLOGY - FROM TIN HYDRIDES TO SILANES

被引:51
作者
CHATGILIALOGLU, C [1 ]
FERRERI, C [1 ]
机构
[1] UNIV NAPOLI,DIPARTIMENTO CHIM ORGAN & BIOL,I-80134 NAPLES,ITALY
关键词
D O I
10.1163/156856793X00361
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Use of organosilanes that promote the Barton-McCombie deoxygenation is an emerging methodology for organic transformations. A comparison between a variety of substituted silanes is presented. (Me(3)Si)(3)SiH rivals Bu(3)SnH in efficiency and it is a superior reagent from ecological and practical perspectives.
引用
收藏
页码:755 / 775
页数:21
相关论文
共 77 条
[1]   ON THE MECHANISM OF REDUCTIVE DEGRADATION OF DITHIOCARBONATES BY TRIBUTYLSTANNANE [J].
BACHI, MD ;
BOSCH, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1517-1519
[2]   TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS [J].
BALLESTRI, M ;
CHATGILIALOGLU, C ;
CLARK, KB ;
GRILLER, D ;
GIESE, B ;
KOPPING, B .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :678-683
[3]   ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS WITH LOW HYDROGEN DONATING ABILITIES [J].
BALLESTRI, M ;
CHATGILIALOGLU, C ;
GUERRA, M ;
GUERRINI, A ;
LUCARINI, M ;
SECONI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03) :421-425
[4]   ELECTRON-SPIN-RESONANCE IDENTIFICATION OF ALKOXYTHIOCARBONYL RADICALS AS POSSIBLE INTERMEDIATES IN BARTON DEOXYGENATION OF ALCOHOLS [J].
BARKER, PJ ;
BECKWITH, ALJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (11) :683-684
[5]  
BARRETT AGM, 1979, J CHEM SOC PERK T 1, P2378, DOI 10.1039/p19790002378
[6]  
BARRETT AGM, 1977, J CHEM SOC CHEM COMM, P8
[7]  
Barton D. H. R., 1993, HALF CENTURY FREE RA
[8]  
Barton D. H. R., 1990, ALDRICHIM ACTA, V23, P3
[9]   ON THE MECHANISM OF DEOXYGENATION OF SECONDARY ALCOHOLS BY TIN HYDRIDE REDUCTION OF METHYL XANTHATES AND OTHER THIOCARBONYL DERIVATIVES [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1990, 31 (28) :3991-3994
[10]  
BARTON DHR, 1991, SYNLETT, P435