SYNTHESIS OF CYCLIC AND ACYCLIC ENOL ETHERS (VINYL ETHERS)

被引：79
|
作者：
GASSMAN, PG
BURNS, SJ
PFISTER, KB
机构：
[1] Department of Chemistry, University of Minnesota, Minneapolis
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 06期
关键词：
D O I：
10.1021/jo00058a027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general method has been developed for the conversion of both cyclic and acyclic acetals of cyclic ketones, acyclic ketones, and aldehydes into enol ethers through treatment of the acetal with trimethylsilyl triflate in the presence of N,N-diisopropylethylamine. The range of isolated yields of enol ethers from the various classes of acetals was as follows: cyclic acetals of cyclic ketones, 83-98%; acyclic acetals of ketones, 72-94%; acyclic and cyclic acetals of aldehydes, 65-90%.
引用
收藏
页码：1449 / 1457
页数：9
相关论文
共 50 条
  • [1] Reactivity of nitrovinylquinones with cyclic and acyclic enol ethers
    Noland, WE
    Kedrowski, BL
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24): : 8366 - 8373
  • [2] A NEW SYNTHESIS OF ACYCLIC ENOL ETHERS
    PFISTER, KB
    GASSMAN, PG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 62 - CHED
  • [3] Aminoalkylation of cyclic and acyclic alkyl vinyl ethers
    Merla, B
    Risch, N
    JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1999, 341 (05): : 472 - 476
  • [4] Stereoselective synthesis of allyl vinyl ethers from silyl enol ethers
    Maeda, K
    Shinokubo, H
    Oshima, K
    Utimoto, K
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07): : 2262 - 2263
  • [5] THE REACTION OF ACYLOXYSULFONIUM SALT WITH CYCLIC ENOL ETHERS - NOVEL SYNTHESIS OF VINYL SULFIDES
    JAIN, S
    SHUKLA, K
    MUKHOPADHYAY, A
    SURYAWANSHI, SN
    BHAKUNI, DS
    SYNTHETIC COMMUNICATIONS, 1990, 20 (09) : 1315 - 1320
  • [6] GENERAL-METHOD FOR THE SYNTHESIS OF ENOL ETHERS (VINYL ETHERS) FROM ACETALS
    GASSMAN, PG
    BURNS, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23): : 5574 - 5576
  • [7] Review of the synthesis of acyclic and cyclic oxime ethers
    Mirjafary, Zohreh
    Abdoli, Morteza
    Saeidian, Hamid
    Kakanejadifard, Ali
    Farnia, S. Morteza F.
    RSC ADVANCES, 2016, 6 (21) : 17740 - 17758
  • [8] Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers
    Jessop, CM
    Parsons, AF
    Routledge, A
    Irvine, DJ
    TETRAHEDRON LETTERS, 2004, 45 (26) : 5095 - 5098
  • [9] Cationic polymerization of vinyl ethers in the presence of silyl enol ethers
    Lang, WH
    Sarker, PK
    Rimmer, S
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2004, 205 (08) : 1011 - 1020
  • [10] STUDIES OF THE ZINC(II) CATALYZED ADDITION OF SILYL ENOL ETHERS TO CYCLIC ENOL ETHERS
    STUDLEY, JR
    WILLS, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) : C3 - C5
12345