Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers

被引：41
|
作者：
Kim, JD
Han, G
Jeong, LS
Park, HJ
Zee, OP
Jung, YH [1 ]
机构：
[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea
[2] Korea Res Inst Biosci & Biotechnol, Taejon 305333, South Korea
[3] Ewha Womans Univ, Coll Pharm, Seoul 120750, South Korea
来源：
TETRAHEDRON | 2002年 / 58卷 / 22期
关键词：
chlorosulfonyl isocyanate; stability of carbocation; ether; carbamate;
D O I：
10.1016/S0040-4020(02)00413-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2degrees and allyl carbocations in that order. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4395 / 4402
页数：8
相关论文
共 50 条
  • [31] Stereoselective Amination of Chiral Benzylic Ethers Using Chlorosulfonyl Isocyanate: Total Synthesis of (+)-Sertraline
    Lee, Sang Hwi
    Kim, In Su
    Li, Qing Ri
    Dong, Guang Ri
    Jeong, Lak Shin
    Jung, Young Hoon
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24): : 10011 - 10019
  • [32] Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate-sodium hydroxide
    Kim, JD
    Han, G
    Zee, OP
    Jung, YH
    TETRAHEDRON LETTERS, 2003, 44 (04) : 733 - 735
  • [33] Novel synthetic method for allylic amination of cyclic allylic ethers using chlorosulfonyl isocyanate
    Lee, Sang Hwi
    Kim, In Su
    Li, Qing Ri
    Dong, Guang Ri
    Jung, Young Hoon
    TETRAHEDRON LETTERS, 2011, 52 (16) : 1901 - 1904
  • [34] CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE ON STILBENE
    FRIEDRICH, HJ
    TETRAHEDRON LETTERS, 1971, (31) : 2981 - +
  • [35] ADDITION OF CHLOROSULFONYL ISOCYANATE TO TETRAPHENYLCYCLOPENTADIENONE
    KUMAR, PR
    SELVI, KT
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1984, 23 (11): : 1046 - 1047
  • [36] Vibrational spectra, conformational stability and ab initio calculations of chlorosulfonyl isocyanate
    Durig, JR
    Zhou, L
    Gounev, TK
    Guirgis, GA
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1997, 53 (10) : 1581 - 1593
  • [37] THE REACTION OF CHLOROSULFONYL ISOCYANATE WITH EPOXIDES - A NOVEL CONVERSION OF EPOXIDES TO CYCLIC CARBONATES
    MURTHY, KSK
    DHAR, DN
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (06) : 1721 - 1725
  • [38] Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate-sodium hydroxide.
    Kim, JD
    Han, GH
    Zee, OP
    Jung, YH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U227 - U227
  • [39] Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl isocyanate
    Kim, JD
    Lee, MH
    Lee, MJ
    Jung, YH
    TETRAHEDRON LETTERS, 2000, 41 (26) : 5073 - 5076
  • [40] Synthetic method for N-allylcarbamates and allyl carbamates: Study on the stability of carbocations using CSI reaction with ethers.
    Jung, YH
    Kim, JD
    Lee, MH
    Zee, OP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U192 - U192
12345