Reactions of asymmetrically substituted O-quinones: 3,5-di-tert-butyl-1,2-benzoquinone with triphenyl-phosphine, -arsine, -stibine, their oxides and trialkyl phosphates

被引:5
作者
Abdou, WM [1 ]
Elkhoshneih, YO [1 ]
Kamel, AA [1 ]
机构
[1] Natl Res Ctr, Dept Pest Chem, Cairo, Egypt
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1997年 / 126卷
关键词
asymmetrically o-quinones; (dioxy)phosphorane; (dioxy)arsinane; stibine-; methylene; hydrogen-bonded formulation; aryl dealkylation;
D O I
10.1080/10426509708043547
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The entitled quinone 4 reacts with triphenylphosphine (3a) and triphenylarsine (3b) to give the cyclic products 12a and 12b, respectively. The same quinone reacts with triphenylstibine (3c) to yield the stibine-methylene 17, The reaction of oxides of 3a-c (5a-c) and trialkyl phosphates 6a-c with the same quinone 4 affords hydrogen bonded complexes 13a-c and o-quinol monophosphates 23a-c, respectively. In both cases compound 22 is the other product. Possible reaction mechanisms are proposed to explain the formation of the new adducts.
引用
收藏
页码:75 / 88
页数:14
相关论文
共 26 条
[1]   INHIBITION OF PSEUDOROTATION IN SOME MONOCYCLIC PENTAOXYPHOSPHORANES [J].
ABDOU, WM ;
DENNEY, DB ;
DENNEY, DZ ;
PASTOR, SD .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 22 (01) :99-107
[2]   ON THE PREPARATION AND PSEUDOROTATION OF CERTAIN MONOCYCLIC PENTAOXYPHOSPHORANES [J].
ABDOU, WM ;
MAHRAN, MR .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1986, 26 (01) :119-127
[3]   FURTHER-STUDIES ON THE BEHAVIOR OF 3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE TOWARD PHOSPHORUS YLIDES [J].
ABDOU, WM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 66 (1-4) :285-287
[4]   THE REACTION OF ALKYL PHOSPHITES WITH 3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE - VARIABLE TEMPERATURE NMR-STUDIES ON NEW PENTAOXYPHOSPHORANES [J].
ABDOU, WM ;
MAHRAN, MRH ;
HAFEZ, TS ;
SIDKY, MM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1986, 27 (03) :345-353
[5]  
ABDOU WM, 1996, J CHEM RES M, P1841
[6]  
ALKATHLAN HZ, 1991, PHOSPHORUS SULFUR, V61, P367
[7]   AROMATIC MOLECULAR CMPLEXES OF THE ELECTRON DONOR-ACCEPTOR TYPE [J].
ANDREWS, LJ .
CHEMICAL REVIEWS, 1954, 54 (05) :713-776
[8]  
BOEKESTEIN G, 1974, RECL TRAV CHIM PAY B, V93, P69
[9]  
CRUTCHFIELD MM, 1967, P31 NUCL MAGNETIC RE, P227
[10]   ALPHA-SUBSTITUTED PHOSPHONATES .58. DIRECT NUCLEAR PHOSPHORYLATION OF 7,7-BIS-PHOSPHORYLATED QUINONE METHIDES WITH TRIVALENT P-H COMPOUNDS DURING C-C SPLITTING [J].
GROSS, H ;
KEITEL, I ;
COSTISELLA, B .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 62 (1-4) :35-45