The synthesis of new organophosphorus compounds via michaelis-arbuzov rearrangment

Chin. J. Org. Chem. ›› 1993, Vol. 13 ›› Issue (3): 278-281. Previous Articles Next Articles

Original Articles

通过Michaelis-Arbuzov重排合成新型

金桂玉;吴海锟;倪海音

南开大学元素有机化学研究所

发布日期:1993-06-25

The synthesis of new organophosphorus compounds via michaelis-arbuzov rearrangment

JIN GUIYU;WU HAIKUN;NI HAIYIN

Published:1993-06-25

Abstract

The Michaelis-Arbuzov reactions of BrCH2COCMe3 or 3-(substituted vinyl)-2,2-dimethylcyclopropanecarbonyl chlorides with phosphites (RO)2P(OR') afford (RO)2P(O)CH2COCMe3 (e.g., R = Me, Et, Bu) in 25.3-81.9% yield and (RO)2P(O)COCH2CH[C(:CH2)Me]CH:CX2 (e.g., R = Me, X = Me or Br) in 42.1-81.4% yield., resp. Bromination (Br2, NaOAc, AcOH) of (RO)2P(O)CH2COCMe3 afforded (RO)2P(O)CHBrCOCMe3 in 40.1-66.1% yield. The phosphonates (EtO)(iPrNH)P(O)CH2COCMe3 and (MeO)(Et2N)P(O)CH2COCMe3 were also prepared

Key words: PHOSPHONIC ACID ESTER, BROMINATION REACTION, PHOSPHOROUS ACID ESTER, ACYL CHLORIDES, CYCLOPROPANE CARBOXYLIC ACID P, REARRANGEMENT REACTION, HEXANONE P

CLC Number:

O627

Cite this article

JIN GUIYU;WU HAIKUN;NI HAIYIN. The synthesis of new organophosphorus compounds via michaelis-arbuzov rearrangment[J]. Chin. J. Org. Chem., 1993, 13(3): 278-281.

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通过Michaelis-Arbuzov重排合成新型

The synthesis of new organophosphorus compounds via michaelis-arbuzov rearrangment

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