REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .14. DEOXYGENATION OF AROMATIC C-NITROSO-COMPOUNDS BY TRIETHYL PHOSPHITE AND TRIPHENYLPHOSPHINE - A NEW CYCLISATION REACTION
REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .14. DEOXYGENATION OF AROMATIC C-NITROSO-COMPOUNDS BY TRIETHYL PHOSPHITE AND TRIPHENYLPHOSPHINE - A NEW CYCLISATION REACTION
复制标题
DOI：
10.1039/jr9630000042
复制
发表时间：
1963-01-01
期刊：
影响因子：
--
通讯作者：
CADOGAN, JIG
中科院分区：
文献类型：
--
作者：
BUNYAN, PJ;CADOGAN, JIG
亚磷酸三乙酯和三苯基膦容易使芳香族C-亚硝基化合物脱附。因此，亚硝基苯和邻乙基亚硝基苯生成相应的氧化偶氮苯;对二甲氨基亚硝基苯生成4，4 '-双二甲氨基氧化偶氮苯和N-对二甲氨基苯基亚磷酰亚胺三乙酯; Z-亚硝基苯和相关化合物发生关环反应生成相应的咔唑。这些反应被认为是通过缺电子氮中间体（氮烯）进行的。
Triethyl phosphite and triphenylphosphine readily deoxygenate aromatic C-nitroso-compounds. Thus, nitrosobenzene and o-ethylnitrosobenzene give the corresponding azoxybenzenes; pdimethylaminonitrosobenzene gives 4, 4’-bisdimethylaminoazoxybenzene and triethyl Np-dimethylaminophenylphosphorimidate; Z-nitrosobiphenyl and related compounds undergo ring closure to the corresponding carbazoles. These reactions are considered to proceed by way of electron-deficient nitrogen intermediates (azenes).