BIS(TERT-BUTYLSULFONYL)ACETYLENE AS A GENERAL SYNTHETIC EQUIVALENT OF ALKYNES IN DIELS-ALDER CHEMISTRY .2. REDUCTIVE AND ALKYLATIVE DESULFONYLATIONS OF BICYCLIC 1-ALKYL-2-(TERT-BUTYLSULFONYL)ETHENES

被引：19

作者：

VIRGILI, M ^{[1
]}

BELLOCH, J ^{[1
]}

MOYANO, A ^{[1
]}

PERICAS, MA ^{[1
]}

RIERA, A ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,MARTI & FRANQUES 1-11,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

D O I：

10.1016/0040-4039(91)80045-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both reductive and alkylative desulfonylations of bicyclic vinyl sulfones derived from Diels-Alder cycloadducts of bis(tert-butylsulfonyl)acetylene (1) are described. These transformations establish the synthetic equivalence of 1 with acetylene, 1-alkynes and internal alkynes in Diels-Alder chemistry.

引用

页码：4583 / 4586

页数：4

共 22 条

[1] SYNTHESES WITH SULFONES .48. STEREOSELECTIVE SYNTHESIS OF 2-ISOPROPYL- 1,4-DIENES THROUGH THE IRON-CATALYZED CROSS-COUPLING REACTION OF 2-BENZENESULFONYL- 1,4-DIENES AND ISOPROPYLMAGNESIUM CHLORIDE [J].

ALVAREZ, E ;

CUVIGNY, T ;

DUPENHOAT, CH ;

JULIA, M .

TETRAHEDRON, 1988, 44 (01) :111-118

[2] 1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC-SYNTHESIS - THE PREPARATION OF ALKYL-SUBSTITUTED AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION-GRIGNARD REACTION-DESULFONYLATION SEQUENCE [J].

AZZENA, U ;

COSSU, S ;

DELUCCHI, O ;

MELLONI, G .

TETRAHEDRON LETTERS, 1989, 30 (14) :1845-1848

[3] BIS(TERT-BUTYLSULFONYL)ACETYLENE AS A GENERAL SYNTHETIC EQUIVALENT OF ALKYNES IN DIELS-ALDER CHEMISTRY .1. HIGHLY SELECTIVE REDUCTION AND ALKYLATING MONODESULFONYLATION OF Z-1,2-BIS(TERT-BUTYLSULFONYL)ETHENES [J].

BELLOCH, J ;

VIRGILI, M ;

MOYANO, A ;

PERICAS, MA ;

RIERA, A .

TETRAHEDRON LETTERS, 1991, 32 (35) :4579-4582

[4] SYNTHESIS USING SULFONES .24. STEREOSELECTIVE SYNTHESIS OF OLEFINS BY HYDROGENOLYSIS OF VINYLSULFONES [J].

BREMNER, J ;

JULIA, M ;

LAUNAY, M ;

STACINO, JP .

TETRAHEDRON LETTERS, 1982, 23 (32) :3265-3266

[5] DIENOPHILIC PROPERTIES OF PHENYL VINYL SULFONE AND TRANS-1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHYLENE - THEIR UTILIZATION AS SYNTHONS FOR ETHYLENE, 1-ALKENES, ACETYLENE, AND MONOSUBSTITUTED ALKYNES IN THE CONSTRUCTION OF FUNCTIONALIZED 6-MEMBERED RINGS VIA [4 + 2] PI-CYCLOADDITION METHODOLOGY [J].

CARR, RVC ;

WILLIAMS, RV ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4976-4986

[6]

CUVIGNY T, 1986, RECL TRAV CHIM PAY B, V105, P409

[7] ETHYNYL PARA-TOLYL SULFONE AS AN ACETYLENE EQUIVALENT IN DIELS-ALDER REACTIONS [J].

DAVIS, AP ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (13) :639-640

[8]

DELUCCHI O, 1984, TETRAHEDRON, V40, P2585

[9] THE ROLE OF SULFUR FUNCTIONALITIES IN ACTIVATING AND DIRECTING OLEFINS IN CYCLO-ADDITION REACTIONS [J].

DELUCCHI, O ;

PASQUATO, L .

TETRAHEDRON, 1988, 44 (22) :6755-6794

[10] REACTIVITY OF PHENYL(TOLYLSULFONYL)ACETYLENE TOWARDS DIENES AND HOMO-DIENES - CYCLO-ADDITIONS VERSUS FRAGMENTATION-ADDITION REACTIONS [J].

DELUCCHI, O ;

LICINI, G ;

PASQUATO, L ;

SENTA, M .

TETRAHEDRON LETTERS, 1988, 29 (07) :831-834

← 1 2 3 →