Proazaphosphatrane P(RNCH2CH2)3N (R=Me, i-Pr)-catalyzed isomerization of allylaromatics, allyl phenyl sulfide, allyl phenyl sulfone, and bis-allylmethylene double bond-containing compounds

被引:14
作者
Yu, ZK
Yan, SG
Zhang, GT
He, W
Wang, LD
Li, Y
Zeng, FL
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, Dept Chem, Dalian 116024, Liaoning, Peoples R China
关键词
allylic compounds; isomerization; methylene-interrupted diene compounds; proazaphosphatrane; P(RNCH2CH2)(3)N;
D O I
10.1002/adsc.200505224
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Using a proazaphosphatrane catalyst, P(RNCH2CH2)(3)N (R=Me, i-Pr), allylaromatics and allyl phenyl sulfide were selectively isomerized to the corresponding vinyl isomers in yields up to > 99% in CH3CN at 40 degrees C. Efficient transformation of allyl phenyl sulfone at ambient temperature afforded an isomerization/dimerization product in > 95% yield. Conjugation of bis-allylmethylene double bond-containing compounds gave the corresponding conjugated isomers for cis,cis-9,12-octadecadienol and its methyl ether in yields up to 97%, and desilylation/conjugation products were obtained from the catalytic reaction of the trimethylsilyl ether of cis,cis-9,12-octadecadienol. The reaction mechanism is discussed based upon the H-1 and P-31 NMR-monitored reactions in CD3CN or CH3CN under the reaction conditions.
引用
收藏
页码:111 / 117
页数:7
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