5-氯-10,11-二氢-5 - H -二苯并[a, d]环庚烯-5,10-硫醚和-5,11-二氯-10,11-二氢-5 - H -二苯并[a, d]环庚烯-5,10-硫醚的合成及其氧化

Sulfur Letters Pub Date : 2002-01-01 DOI:10.1080/02786110211428

M. Hegab, A. El-Gazzar, I. Farag, F. A. Gad

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引用次数: 4

摘要

5-硫氧基-10,11-二氢-5 H -二苯并[a,d]环庚烯2a氯化得到5-氯-10,11-二氢-5 H -二苯并[a,d]环庚烯-5,10-硫4。氯化5-硫氧基-5 H -二苯并[a,d]环庚烯2b得到顺式和反式两种异构体-5,11-二氯-10,11-二氢-5 H -二苯并[a,d]环庚烯-5,10-硫7a,b。两种硫化物4和7a,b分别用mCPBA或h2o2 /AcOH氧化得到相应的亚砜5和8a,b。硫化物7a,b用KI处理得到伯酮1b和反式-5-氯-11-羟基-10,11-二氢-5- H -二苯并[a,d]环庚烯-5,10-硫化物9。通过不同的光谱技术以及化合物4和9的单晶x射线衍射确定了新化合物的结构。

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Synthesis of 5-Chloro-10,11-Dihydro-5 H -Dibenzo[ a , d ]Cycloheptene-5,10-Sulfide and -5,11-Dichloro-10,11-Dihydro-5 H -Dibenzo[ A , D ]Cycloheptene-5,10-Sulfide and their Oxidation

The chlorination of 5-thioxo-10,11-dihydro-5 H -dibenzo[ a,d ]cycloheptene 2a gave 5-chloro-10,11-dihydro-5 H -dibenzo[ a,d ]cycloheptene-5,10-sulfide 4 . Chlorination of 5-thioxo-5 H -dibenzo[ a,d ]cycloheptene 2b gave the two isomers cis - and trans -5,11-dichloro-10,11-dihydro-5 H -dibenzo[ a,d ]cycloheptene-5,10-sulfide 7a,b . The two sulfides 4 and 7a,b were oxidized by using mCPBA or H 2 O 2 /AcOH to give the corresponding sulfoxides 5 and 8a,b , respectively. Treatment of the sulfide 7a,b with KI gave the primary ketone 1b together with trans -5-chloro-11-hydroxy-10,11-dihydro-5 H -dibenzo[ a,d ]cycloheptene-5,10-sulfide 9 . The structures of the new compounds were established by different spectroscopic techniques as well as single crystal X-ray diffraction for compounds 4 and 9 .

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Sulfur Letters

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