Cooperative Effect of Carborane and Pyridine in the Reaction of Carboranyl Alcohols with Thionyl Chloride: Halogenation versus Oxidation

被引：23

作者：

Terrasson, Vincent ^{[1
,2
]}

Planas, Jose G. ^{[2
]}

Prim, Damien ^{[1
]}

Vinas, Clara ^{[2
]}

Teixidor, Francesc ^{[2
]}

Light, Mark E. ^{[3
]}

Hursthouse, Michael B. ^{[3
]}

机构：

[1] Univ Versailles St Quentin en Yvelines, CNRS, Inst Lavoisier Versailles, UMR 8180, F-78035 Versailles, France

[2] CSIC, Inst Ciencia Mat Barcelona, Bellaterra 08193, Spain

[3] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/jo801672f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a,b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a,b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl- 1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.

引用

页码：9140 / 9143

页数：4

共 50 条

[31] EFFECT OF STRUCTURE OF ALIPHATIC-ALCOHOLS ON THEIR REACTIVITY .1. REACTION OF ALCOHOLS WITH PARA NITROBENZOYL CHLORIDE
BABAEVA, LG
BOGATKOV, SV
KRUGLIKO.RI
UNKOVSKI.BV
ZHURNAL ORGANICHESKOI KHIMII, 1974, 10 (02): : 250 - 254
[32] 1,3-BRIDGED AROMATIC SYSTEMS .14. EFFECT OF CONFIGURATION ON COURSE OF REACTIONS OF ALCOHOLS WITH THIONYL CHLORIDE AND WITH PHOSGENE
PARHAM, WE
SAYED, Y
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (21): : 3142 - 3143
[33] Atypical oxidation reaction by thionyl chloride:: Easy two-step synthesis of N-alkyl-1,4-dithiines
Valla, Alain
Cartier, Dominique
Zentz, Frederic
Labia, Roger
SYNTHETIC COMMUNICATIONS, 2006, 36 (23) : 3591 - 3597
[34] Effect of stannous chloride on low-temperature oxidation reaction of coal
Qin, Botao
Dou, Guolan
Zhong, Xiaoxing
FUEL PROCESSING TECHNOLOGY, 2018, 176 : 59 - 63
[35] Thionyl chloride/pyridine system as a condensing agent for the polyesterification reaction of N,N′-(4,4′-oxydiphthaloyl)-bis-L-leucine and aromatic diols
Mallakpour, Shadpour
Kowsari, Elahch
IRANIAN POLYMER JOURNAL, 2006, 15 (06) : 457 - 465
[36] Understanding the reaction mechanisms of Pd-catalysed oxidation of alcohols and domino oxidation-arylation reactions using phenyl chloride as an oxidant
Li, Yang
Lin, Zhenyang
ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (10): : 1188 - 1196
[37] Thionyl chloride/pyridine system as a condensing agent for the polyesterification reaction of N,N′-(4,4′-oxydiphthaloyl)-bis-L- leucine and aromatic diols
Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan-84156/83111, Iran
Iran Polym J Eng Ed, 2006, 6 (457-465):
[38] Reaction of O,O-dialkyl alkylphosphonates with thionyl chloride. A remarkable effect of the O-(2-dialkylamino)ethyl substituent
Pienaar, A
Modro, AM
Modro, TA
HETEROATOM CHEMISTRY, 1996, 7 (03) : 177 - 181
[39] Reaction of O,O-Dialkyl Alkylphosphonates with Thionyl Chloride. A Remarkable Effect of the O-(2-Dialkylamino)ethyl Substituent
Heteroatom Chem, 3 (177):
[40] CHARACTERIZATION OF A NOVEL LOW OXIDATION-STATE TRANSITION-METAL PEROXIDE FROM REACTION OF COPPER(I) CHLORIDE WITH OXYGEN IN PYRIDINE
KRAMER, CE
DAVIES, G
DAVIS, RB
SLAVEN, RW
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) : 606 - 607

← 1 2 3 4 5 →