Reaction of arylphosphines with singlet oxygen: Intra- vs intermolecular oxidation

被引：44

作者：

Gao, RM ^{[1
]}

Ho, DG ^{[1
]}

Dong, T ^{[1
]}

Khuu, D ^{[1
]}

Franco, N ^{[1
]}

Sezer, O ^{[1
]}

Selke, M ^{[1
]}

机构：

[1] Calif State Univ Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90032 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol010195v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The chemistry of singlet oxygen with all three isomers of tris(methoxyphenyl)phosphine has been studied. For the severely hindered ortho isomer, intramolecular rearrangement to form phenyl diphenyl phosphinate is preferred to formation of phosphine oxide at low concentration in aprotic solvents. In protic solvents, no intramolecular reactivity is observed. A detailed kinetic analyses has been undertaken. There is no physical quenching, regardless of solvent. Mechanistic implications of these findings are discussed.

引用

页码：3719 / 3722

页数：4

共 13 条

[1] AUTOXIDATION OF TRIALKYLPHOSPHINES
BUCKLER, SA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (16) : 3093 - &
[2] CRABTREE RH, 1988, ORGANOMETALLIC CHEM, P72
[3] Foote C. S., 1971, IUPAC C 23 SPEC LEC, V4, P129
[4] CHEMISTRY OF SINGLET OXYGEN .35. NATURE OF INTERMEDIATES IN THE PHOTO-OXYGENATION OF SULFIDES
GU, CL
FOOTE, CS
KACHER, ML
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (19) : 5949 - 5951
[5] Higgens R., 1968, ADV CHEM SER, V77, P102
[6] Hirsivaara L, 2000, INORG CHIM ACTA, V307, P47
[7] Reaction of organic sulfides with singlet oxygen. A revised mechanism
Jensen, F
Greer, A
Clennan, EL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4439 - 4449
[8] CHEMISTRY OF SINGLET OXYGEN .45. MECHANISM OF THE PHOTO-OXIDATION OF SULFIDES
LIANG, JJ
GU, CL
KACHER, ML
FOOTE, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) : 4717 - 4721
[9] STRUCTURES AND ENERGIES OF INTERMEDIATES IN THE REACTIONS OF SINGLET OXYGEN WITH ORGANIC PHOSPHINES AND SULFIDES
NAHM, K
LI, Y
EVANSECK, JD
HOUK, KN
FOOTE, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) : 4879 - 4884
[10] NAHM K, 1989, J AM CHEM SOC, V111, P909

← 1 2 →