MECHANISM OF AUTOXIDATION OF TRIALKYLBORANES

被引:47
作者
ALLIES, PG
BRINDLEY, PB
机构
[1] Kingston College of Technology, Kingston upon Thames, Surrey
来源
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC | 1969年 / 09期
关键词
D O I
10.1039/j29690001126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The autoxidation of butylboranes and related compounds are considered and the evidence favouring a free-radical chain mechanism is described. Analogies with hydrocarbon autoxidations were observed particularly towards antioxidants known to react with peroxy-radicals. Inhibition by galvinoxyl gives some information about the easy initiation step. The rapid propagation step was affected by nitroxide radicals and a nitroxide-alkyl radical adduct was isolated. (+)-Di-isopinocampheyl-s-butylborane was comparatively stable in contact with diborane and autoxidised with extensive racemisation of the butyl group.
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页码:1126 / &
相关论文
共 33 条
[1]   PEROXIDES OF ELEMENTS OTHER THAN CARBON .3. THE FORMATION OF BORON PEROXIDES BY AUTOXIDATION [J].
ABRAHAM, MH ;
DAVIES, AG .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JAN) :429-438
[2]  
ALLIES PG, 1968, CHEM IND-LONDON, P1439
[3]  
ALLIES PG, 1967, CHEM IND-LONDON, P319
[4]   PHYSICAL AND CHEMICAL PROPERTIES OF ORGANO-METALLIC COMPOUNDS .3. THE OXIDATION OF BORON AND ANTIMONY ALKYLS [J].
BAMFORD, CH ;
NEWITT, DM .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (AUG) :695-701
[5]   GALVINOXYL (2,6-DI-TERT-BUTYL-ALPHA-(3,5-DI-TERT-BUTYL-4-OXO-2,5-CYCLOHEXADIENE-1-YLIDENE)-P-TOLYLOXY) AS A SCAVENGER OF SHORTER-LIVED FREE RADICALS [J].
BARTLETT, PD ;
FUNAHASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (13) :2596-&
[6]  
BAWN CEH, 1959, P CHEM SOC LONDON, P397
[7]   REACTION OF ORGANOBORANES WITH NEUTRAL HYDROGEN PEROXIDE [J].
BIGLEY, DB ;
PAYLING, DW .
CHEMICAL COMMUNICATIONS, 1968, (16) :938-&
[8]  
BRIERE R, 1965, B SOC CHIM FR, P3273
[9]  
BRINDLEY PB, 1968, POLYMER LETTERS, V6, P831
[10]  
BROWN HC, 1961, J AM CHEM SOC, V83, P486, DOI 10.1021/ja01463a054