PEROXIDES OF ELEMENTS OTHER THAN CARBON .15. AUTOXIDATION OF EPIMERIC TRINORBORNYLBORANES

被引：66

作者：

DAVIES, AG

ROBERTS, BP

机构：

[1] William Ramsay and Ralph Forster Laboratories, University College

来源：

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC | 1969年 / 03期

关键词：

D O I：

10.1039/j29690000311

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three epimeric mixtures of trinorbornylboranes have been prepared, in which the percentages of exo- and endonorbornyl groups are 99.2 and 0.8%, 66 and 34%, and 14 and 86%, respectively. All three react with oxygen to give norbornylbis(norbornylperoxy)borane containing about 76% exo- and 24% endo-norbornyl-oxygen links, and the reactions are inhibited by galvinoxyl, copper NN-dibutyldithiocarbamate, and phenothiazine. It is proposed that the autoxidations follow a homolytic chain mechanism involving a common norbornyl radical.

引用

收藏

页码：311 / &

相关论文

共 17 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, 1967, CHEM IND-LONDON, P319

[3] 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-&

[4] PROTONOLYSIS AND DEUTEROLYSIS OF TRI-2-NORBORNYLBORANE-EVIDENCE FOR RETENTION OF CONFIGURATION IN PROTONOLYSIS OF ORGANOBORANES [J].

BROWN, HC ;

MURRAY, KJ .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (02) :631-&

[5] HYDROBORATION .9. HYDROBORATION OF CYCLIC AND BICYCLIC OLEFINS-STEREOCHEMISTRY OF HYDROBORATION REACTION [J].

BROWN, HC ;

ZWEIFEL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (11) :2544-&

[6] BRIDGED POLYCYCLIC COMPOUNDS .17. STEREOCHEMISTRY OF CONVERSIONS OF SOME SUBSTITUTED NORBORNANECARBOXYLIC ACIDS TO SUBSTITUTED NORBORNYL BROMIDES [J].

CRISTOL, SJ ;

KRALL, RE ;

DOUGLASS, JR ;

FIRTH, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (08) :2711-&

[7] PEROXIDES OF ELEMENTS OTHER THAN CARBON .12. AUTOXIDATION OF OPTICALLY ACTIVE 1-PHENYLETHYLBORONIC ACID [J].

DAVIES, AG ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1967, (01) :17-&

[8] PEROXIDES OF ELEMENTS OTHER THAN CARBON .14. MECHANISM OF AUTOXIDATION OF ORGANIC COMPOUNDS OF LITHIUM MAGNESIUM ZINC CADMIUM AND ALUMINIUM [J].

DAVIES, AG ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (09) :1074-&

[9] ORGANOMETALLIC REACTIONS .11. STEREOCHEMISTRY OF OXIDATIVE AND HYDROLYTIC CLEAVAGE OF 1-PHENYLETHYL-BORON BOND [J].

DAVIES, AG ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (12) :1474-&

[10] NUCLEAR MAGNETIC RESONANCE SPECTRA OF 2,7-DIOXABICYCLO[2,2,1]HEPTANES [J].

GAONI, Y .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (04) :382-&