One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis

被引：52

作者：

Ballini, R ^{[1
]}

Bosica, G ^{[1
]}

Fiorini, D ^{[1
]}

Palmieri, A ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

SYNTHESIS-STUTTGART | 2004年 / 12期

关键词：

1,3-dinitroalkanes; Michael additions; heterogeneous catalysis; alumina; one-pot;

D O I：

10.1055/s-2004-829160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of aldehydes with an excess of nitromethane in the presence of basic alumina as solid catalyst allows the one pot preparation of 1,3-dinitroalkanes. The synthesis proceeds through the nitroaldol reaction of nitromethane, which acts both as nucleophile and as solvent, to the aldehydes with the formation of beta-nitroalkanols as intermediates that convert to nitroalkenes. Further nucleophilic behavior of the nitromethane produces the in situ conjugate addition of its carbanion to the formed nitroalkenes giving the one-pot synthesis of the title compounds. The catalyst shows general applicability with aliphatic, aromatic and heteroaromatic aldehydes.

引用

页码：1938 / 1940

页数：3

共 31 条

[1]

Alcantara MPD, 1996, SYNTHESIS-STUTTGART, P64

[2] SYNTHESIS OF 1,3,3-TRINITROAZETIDINE VIA THE OXIDATIVE NITROLYSIS OF N-P-TOSYL-3-AZETIDINONE OXIME [J].