Three syntheses of trans-cyclooctane-1,2-dithiol by ring opening of cis-cyclooctene episulfoxide with ammonium thiocyanate followed by reduction and reductions of trans-1,2-di(thiocyanato)cyclooctane and trans-1,2-cyclooctyl trithiocarbonate

Three syntheses of trans-cyclooctane-1,2-dithiol by ring opening of cis-cyclooctene episulfoxide with ammonium thiocyanate followed by reduction and reductions of trans-1,2-di(thiocyanato)cyclooctane and trans-1,2-cyclooctyl trithiocarbonate
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顺式环辛烯环亚砜与硫氰酸铵开环,再还原反式1,2-二(氰硫基)环辛烷和反式1,2-环辛基三硫代碳酸酯,三次合成反式环辛烷-1,2-二硫醇

DOI:
10.1080/17415990902839435
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发表时间:
2009
影响因子:
2.2
通讯作者:
N. Nakata
N. Nakata
中科院分区:
化学4区
文献类型:
--
作者:
A. Ishii;Ayako Ono;N. Nakata

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采用三种方法合成反式环辛烷-1,2-二硫醇:(1)用NH4SCN在四氢呋喃中开环,然后用二异丁基铝氢化物(DIBAH)在己烷中逐步还原,再用LiAlH4在乙醚中还原;(ii)用DIBAH和LiAlH4逐步还原反式-1,2-二(硫氰酸酯)环辛烷11;(iii)用LiAlH4在回流醚中还原反式-1,2-环辛基三硫代碳酸盐。详细考察了方法(1)的反应过程。
trans-Cyclooctane-1,2-dithiol was synthesized by three methods: (i) ring opening of trans-cyclooctene episulfoxide with NH4SCN in THF followed by a stepwise reduction with diisobutylaluminum hydride (DIBAH) in hexane and then LiAlH4 in ether; (ii) a stepwise reduction of trans-1,2-di(thiocyanato)cyclooctane 11 with DIBAH and then LiAlH4; and (iii) the reduction of trans-1,2-cyclooctyl trithiocarbonate with LiAlH4 in refluxing ether. The course of reactions of method (i) was investigated in detail.
DOI: 10.1021/ja072044e
发表时间: 2007-05
影响因子: 15
作者:
J. Nakayama;Y. Tajima;Pi Xue-hua;Y. Sugihara
通讯作者: J. Nakayama;Y. Tajima;Pi Xue-hua;Y. Sugihara