The reactions of α-phosphoryl sulfoxides with ortho- and para-quinones.: Synthesis of α,β-unsaturated sulfoxides and aryl 1,2-x-fused onto furan rings

被引：11

作者：

Abdou, WM ^{[1
]}

Ganoub, NA ^{[1
]}

机构：

[1] Natl Res Ctr, Cairo, Egypt

来源：

SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 19期

关键词：

D O I：

10.1080/00397919808004904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of alpha-phosphoryl sulfoxide 3 with o-quinones 1a-c were found to react in different pathways to give either the mono-olefin 4 (from la) or the corresponding [1,2-x]-fused dihydrofuran 8 (from 1b) or 9 (from 1c). Conversely, a completely different pattern of behaviour was observed for 3 toward the p-quinones 2a and 2b, whereby 2-(4-hydroxyaryl)-1,2-bis(methyl sulfoxide) ethyl diethyl phosphonate derivatives 11 and 12, respectively, were the products.

引用

收藏

页码：3579 / 3589

页数：11

相关论文

共 29 条

[1] REACTION OF PHOSPHONIUM YLIDES WITH 3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE [J].

ABDOU, WM ;

GANOUB, NAF ;

ABDELRAHMAN, NM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 61 (1-2) :91-96

[2] FURTHER-STUDIES ON THE REACTION OF STABLE PHOSPHORUS YLIDES WITH CYCLIC CIS-DISULFIDES [J].

ABDOU, WM ;

HENNAWY, IT .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 89 (1-4) :105-112

[3] Comparative chemical studies of the behavior of 4-cyano-1,2-dithioles in analogy with 1,2,4-dithiazoles toward stable phosphonium ylides [J].

Abdou, WM ;

Ganoub, NAF .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 105 (1-4) :63-71

[4] Reactions of alkylidenephosphoranes with symmetrically substituted p-quinones [J].

Abdou, WM ;

Salem, MAE ;

Sediek, AA .

TETRAHEDRON, 1997, 53 (40) :13945-13958

[5]

Abdou WM, 1997, HETEROCYCL COMMUN, V3, P57

[6] 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

[7] ORGANOPHOSPHORUS CHEMISTRY .22. REACTION OF 3-FORMYL-4-CHROMONE WITH TERVALENT AND PENTA-VALENT PHOSPHORUS-COMPOUNDS [J].

ABDOU, WM ;

KHIDRE, MD ;

MAHRAN, MR .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 61 (1-2) :83-90

[8]

ABDOU WM, 1995, TETRAHEDRON, V51, P11420

[9]

ABDOU WM, 1995, HETEROCYCLIC COMM, V1, P387

[10]

ABDOU WM, 1997, INPRESS J CHEM RES M