SYNTHESIS OF 2-NITRO 1,3-DIENES - USEFUL INTERMEDIATES IN THE PREPARATION OF UNSATURATED 1,4-DICARBONYL COMPOUNDS

被引:21
作者
BACKVALL, JE
KARLSSON, U
CHINCHILLA, R
机构
[1] Department of Organic Chemistry, S-751 21 Uppsala
关键词
D O I
10.1016/0040-4039(91)80097-P
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Nitro 1,3-dienes have been obtained from conjugated dienes via a nitroselenation-elimination sequence. The elimination of the selenium moiety is catalyzed by base. Several of the 2-nitro 1,3-dienes were isolated, whereas others were generated in situ and used for further reaction. They were found to react readily with enol ethers to give nitronic esters, which subsequently were transformed to unsaturated 1,4-dicarbonyl compounds.
引用
收藏
页码:5607 / 5610
页数:4
相关论文
共 34 条
[1]   SULFONYLMERCURATION OF CONJUGATED DIENES - A FACILE ROUTE TO ALLYL-SULFONES AND DIENYL-SULFONES [J].
ANDELL, OS ;
BACKVALL, JE .
TETRAHEDRON LETTERS, 1985, 26 (37) :4555-4558
[3]  
BACK TG, 1989, TETRAHEDRON LETT, V47, P6481
[4]   FACILE CYCLO-ADDITION OF 2-PHENYLSULFONYL 1,3-DIENES TO INDOLES [J].
BACKVALL, JE ;
PLOBECK, NA ;
JUNTUNEN, SK .
TETRAHEDRON LETTERS, 1989, 30 (19) :2589-2592
[5]  
BACKVALL JE, 1987, J AM CHEM SOC, V109, P6396
[6]   SELENOSULFONATION OF 1,3-DIENES - ONE-POT SYNTHESIS OF 2-(PHENYLSULFONYL)-1,3-DIENES [J].
BACKVALL, JE ;
NAJERA, C ;
YUS, M .
TETRAHEDRON LETTERS, 1988, 29 (12) :1445-1448
[7]  
BACKVALL JE, 1988, J ORG CHEM, V53, P2398
[8]   2-PHENYLSULFONYL 1,3-DIENES IN ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ENAMINES AND ENOL ETHERS [J].
BACKVALL, JE ;
RISE, F .
TETRAHEDRON LETTERS, 1989, 30 (39) :5347-5348
[9]  
BACKVALL JE, 1989, ORG SYNTH, V67, P105
[10]   GENERATION AND CYCLOADDITION REACTIONS OF 3-SUBSTITUTED-2-NITRO-1,3-DIENES [J].
BARCO, A ;
BENETTI, S ;
POLLINI, GP ;
SPALLUTO, G ;
ZANIRATO, V .
TETRAHEDRON LETTERS, 1991, 32 (22) :2517-2520