ACETYLENEDICARBALDEHYDE - ISOLATION AND EXCLUSIVE DIENOPHILIC ACTIVITY UNDER NEUTRAL CONDITIONS

被引：49

作者：

GORGUES, A ^{[1
]}

STEPHAN, D ^{[1
]}

BELYASMINE, A ^{[1
]}

KHANOUS, A ^{[1
]}

LECOQ, A ^{[1
]}

机构：

[1] UNIV RENNES 1,SYNTH ORGAN LAB,F-35042 RENNES,FRANCE

来源：

TETRAHEDRON | 1990年 / 46卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)88374-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Procedures for isolating acetylenedicarbaldehyde (ADCA) 1 in the pure state, or for obtaining this unstable compound in diluted aprotic solutions (CH2C12, CCl4, toluene) are detailed. They are based on the acidolysis of its mono-[diEt]-acetal 2a with an excess of formic acid, followed by dehydration of residual acid into carbon monoxide with P205 in CH2C12 diluted solution. Under neutral conditions, ADCA reacts with dienes as dienophile only (4 produced), in sharp contrast to what occurs in acidic medium, where its Michael acceptor character mainly behaves (5 produced) when one starts from aromatic dienes. © 1990.

引用

页码：2817 / 2826

页数：10

共 32 条

[21] FORMIC ANHYDRIDE
OLAH, GA
VANKAR, YD
ARVANAGHI, M
SOMMER, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08): : 614 - 614
[22] RIMMELIN J, 1978, B SOC CHIM FR, V3, P461
[23] SYNTHESIS OF BUTANOIC ACID 4,4'-[(4E, 6Z, "9Z-PENTADECATRIEN-2-YNYLIDENE)]-BIS WITH LEUKOTRIENE-LIKE ACTIVITY - NOVEL ACETYLENIC ACETALS AND DITHIOACETALS AS ANTAGONISTS OF LEUKOTRIENE-C4
SAKSENA, AK
GREEN, MJ
MANGIARACINA, P
WONG, JK
KREUTNER, W
GULBENKIAN, AR
[J]. TETRAHEDRON LETTERS, 1985, 26 (52) : 6427 - 6430
[24] SALLEM, 1989, J CHEM SOC CHEM COMM, P1520
[25] SIMON A, 1989, J CHEM RES-S, P34
[26] SIMON A, 1989, J CHEM RES M, P334
[27] ACETYLENEDICARBALDEHYDE - ISOLATION AND SOME EXAMPLES OF EXCLUSIVE DIENOPHILICITY UNDER NEUTRAL CONDITIONS
STEPHAN, D
GORGUES, A
BELYASMINE, A
LECOQ, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 263 - 264
[28] PREPARATION OF 4,7-DIHYDROISOINDOLE DERIVATIVES AND PRELIMINARY-STUDY OF THEIR REACTIVITY WITH ELECTROPHILIC ALKENES AND ALKYNES
STEPHAN, D
GORGUES, A
LECOQ, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (09) : 1025 - 1028
[29] A FACILE ACCESS TO MASKED ISOBENZOFURANS - HIGH EXO-STEREOSELECTIVITY IN THE DIELS-ALDER REACTIONS OF "4,7-DIHYDRO-4,M-ETHANOISOBENZOFURAN
STEPHAN, D
GORGUES, A
LECOQ, A
[J]. TETRAHEDRON LETTERS, 1986, 27 (36) : 4295 - 4298
[30] STOWELL JC, 1979, SYNTHESIS-STUTTGART, P132

← 1 2 3 4 →