摘要
研究了硫代米氏酮与反-1-苯基-1,3-丁二烯(2a),反-2,4-戊二烯酸甲酯(2b),反-1,3-戊二烯(2c)的环加成反应,硫酮与这些双烯在50～70℃下反应,反应的区域选择性为生成的主要加成物位阻较小,并用前线分子轨道理论及立体化学进行了解释。
The cycloaddition reactions of thiomichler' s ketone( 1) with trans - 1- substituted - 1,3 -butadiene compounds[ 1 - phenyl - 1,3 - buta - diene(2a) ,2,4- methyl pentadienoate(2b), 1,3-pentadiene( 2c ) ] werestudied. The reactions of 1 with 2a and 2b occurred at 50 ℃ andmain cycloadducts(3a) and (3b) were formed. The reaction of 1 with 2c occurred at 70℃ to afford 91% cycloadduct(3c) and 9% isomer(4c). The structures of above adducts are supported by analytical and spectral data. The regioselectivity of 1 with 2a and 2c are con- sistent with the FMO theory. On the other hand, 2b in the reaction with 1 showed the regioselectivity to be different from the FMOtheory prediction, affording 3b but not 4b. In this reaction, the steric hindrance may to be the major regiocontrolling factor.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
1997年第2期183-187,共5页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金
关键词
硫代米氏酮
反式
取代
丁二烯
环加成反应
The cycloaddition reactions, Thiomichler's ketone, Trans - 1 -substituted- 1,3 -butadiene
