REACTIONS OF TETRAZINES WITH UNSATURATED COMPOUNDS - A NEW SYNTHESIS OF PYRIDAZINES
REACTIONS OF TETRAZINES WITH UNSATURATED COMPOUNDS - A NEW SYNTHESIS OF PYRIDAZINES
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DOI：
10.1021/ja01525a060
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发表时间：
1959-01-01
影响因子：
15
通讯作者：
LINDSEY, RV
中科院分区：
文献类型：
--
作者：
CARBONI, RA;LINDSEY, RV
发现3，6-双（多氟烷基）-苯乙烯-四嗪与苯乙烯、丁二烯、乙炔、脂肪族和脂环族烯烃及烯类等不饱和化合物反应生成哒嗪。3，6-二苯基-和3，6-二甲基-嘧啶-四嗪的反应类似，但不太容易。本文讨论了该反应的范围和产物的性质。虽然有许多合成四嗪的路线已被报道，但对它们的化学性质知之甚少。我们最近从氟代烯烃和肼合成1，2-二氢-3，6-双（多氟烷基）均四嗪的研究中发现，这些物质容易与各种不饱和化合物反应，放出一摩尔氮，生成3，6-二取代哒嗪。反应显然是通过四嗪的-C = N-N= C-二烯体系与适当的烯属和炔属亲二烯体的1，4-加成进行的。
3, 6-Bis-(polyfluoroalkyl)-syiM-tetrazines were found to react with remarkable ease with a variety of unsaturated com-pounds, including styrenes, butadienes, acetylenes, aliphatic and alicyclic olefins, and aliene to yield pyridazines. 3, 6-Diphenyl-and 3, 6-dimethyl-rym-tetrazines reacted similarly though less readily. The scope of this reaction and the nature of the products are discussed.Although a number of synthetic routes to tetrazines have been reported, 1 little is known about their chemistry. In connection with our recent studies of the synthesis ofl, 2-dihydro-3, 6-bis-(polyfluoroalkyl)-sym-tetrazines from fluoroólefins and hydrazine, 2 it was discovered that these substances react easily with a variety of unsaturated compounds with the evolution of one mole of nitro-gen to yield 3, 6-disubstituted pyridazines. The reaction apparently proceeds by 1, 4-additionof the—C= N—N= C—diene system of the tetrazine to the appropriate olefinic and acetylenic dienophiles.