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Reaction of Bis[2-hydroxy-1-(2,6-dimethyl-4-methoxyphenyl)ethyl] Ethers with Tosyl Chloride
Bulletin of the Chemical Society of Japan ( IF 3.3 ) Pub Date : 1979-02-01 , DOI: 10.1246/bcsj.52.462
Munehiro Nakatani 1 , Tsunao Hase 1
Affiliation  

In the reaction with tosyl chloride in pyridine, the meso isomer (2a) of bis[2-hydroxy-1-(2,6-dimethyl-4-methoxyphenyl)ethyl] ether rearranged to give arylacetaldehyde (3) and 2-arylmethyl-4-aryl-1,3-dioxolane (4), and the racemic isomer (2b) afforded 3, 4, and 2,6-diaryl-1,4-dioxane. The aryl migration in this reaction has been confirmed by the use of the deuterated compounds, 2a-D and 2b-D, respectively, substituted with deuteriums at the 2,2-positions.

中文翻译:

双[2-羟基-1-(2,6-二甲基-4-甲氧基苯基)乙基]醚与甲苯磺酰氯的反应

在吡啶中与甲苯磺酰氯反应中,双[2-羟基-1-(2,6-二甲基-4-甲氧基苯基)乙基]醚的内消旋异构体(2a)重排得到芳基乙醛(3)和2-芳基甲基- 4-芳基-1,3-二氧戊环(4)和外消旋异构体(2b)得到3、4和2,6-二芳基-1,4-二氧六环。该反应中的芳基迁移已通过使用分别在 2,2-位被氘取代的氘代化合物 2a-D 和 2b-D 得到证实。
更新日期:1979-02-01
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