Derivatives of alpha-phosphorylated aldehydes

Ismailov V., Aydin A., Guseynov F.

TETRAHEDRON, cilt.55, sa.28, ss.8423-8432, 1999 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 55 Konu: 28
  • Basım Tarihi: 1999
  • Doi Numarası: 10.1016/s0040-4020(99)00429-9
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.8423-8432


Conditions for the selective chlorination of a-phosphorylated aldehydes as a means of synthesising alpha-monochloro- and alpha,alpha-dichlorosubstituted derivatives are described. Dichloro derivatives show high reactivity and easily add thiols, amides and ethyleneimine to give stable hemi-thioacetals, hemiamidals and hemiaminal. From the silyl ether of hemiisopropyl thioacetal above 140 degrees C,alpha-ketophosphonate is obtained by the elimination of silane followed by the rearrangement of the oxirane intermediate. Alkylations of a-phosphorylated aldehydes with alkyl bromides gave enol ethers, However, dihalogenoalkanes such as 1,2-dibromoethane or 1,3-dibromopropane yielded phosphatecyclanes along with enol ethers, all in trans configuration, (C) 1999 Elsevier Science Ltd. All rights reserved.