Mode of alkylation of alcohols with O-cyclopropylmethyl trichloroacetimidate and O-cyclobutyl trichloroacetimidate
作者:Ibrahim A. I. Ali、Xiangming Zhu、Es Sayed H. El Ashry、Richard R. Schmidt
DOI:10.3998/ark.5550190.0013.604
日期:——
Acid promoted alkylation of hydroxy group containing acceptors 3-14 with O-cyclopropylmethyl and O-cyclobutyltrichloroacetimidates 1 and 2, respectively, afforded ethers with cyclopropylmethyl, cyclobutyl, and homoallyl residues as a result of the rearrangement of the cation intermediates. The dependence of product formation on acceptor structure is discussed.
We have developed new phosphorylating agents, 3-phosphono-2-(N-cyanoimino)-thiazolidine derivatives (3-phosphono-NCTs), which were readily synthesized by phosphorylation of NCT, and transformed primary and secondary alcohols into phosphates in good yield. The transfer of three kinds of dialkylphosphono groups [(PhO)(2)P(O)-, (EtO)(2)P(O)-, (Cl3CCH2O)(2)P(O)-] proceeded in excellent yields. Selective phosphorylation of various alcohols was also accomplished. (C) 2002 Elsevier Science Ltd. All rights reserved.
BUTSUGAN Y.; TSUKAMOTO H.; MORITO N.; BITO T., CHEM. LETT. 1976, NO 5, 523-524