The nucleophilic ring-opening of N-benzylquinuclidinium bromide

被引：10
|
作者：
Axelsson, O
Peters, D
机构：
[1] NeuroSearch A/S, DK-2600 Glostrup
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1997年 / 34卷 / 02期
关键词：
D O I：
10.1002/jhet.5570340217
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Benzylquinuclidinium bromide was ring opened by a series of heteronucleophiles, in the presence of cesium carbonate, to yield the corresponding N-benzyl-4-(2-hetero-ethyl)piperidines. The best yields were found with thiophenol (56%), phenol (55%), and benzimidazole (38%) as nucleophiles.
引用
收藏
页码：461 / 463
页数：3
相关论文
共 50 条
  • [41] Substituents effect on aziridine chemistry: N-inversion energy, reactivity and regioselectivity of nucleophilic ring-opening
    Park, G
    Kim, SC
    Kang, HY
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (09): : 1339 - 1343
  • [42] STEREOCHEMISTRY OF NUCLEOPHILIC RING-OPENING REACTIONS OF OPTICALLY-ACTIVE N-ACETYL-2-METHOXYCARBONYLAZIRIDINE
    DAVOLI, P
    FORNI, A
    MORETTI, I
    PRATI, F
    TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 2011 - 2016
  • [43] EFFICIENT RING-OPENING OF N-PHENYL-2-OXAZOLIDONES WITH HYDROGEN BROMIDE IN ACETIC-ACID
    LIM, MI
    WEEKS, G
    PAN, YG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 258 - ORGN
  • [44] CONJUGATE NUCLEOPHILIC RING-OPENING OF ACTIVATED VINYLCYCLOPROPANES FACILITATED BY HOMOGENOUS PALLADIUM CATALYSIS
    BURGESS, K
    TETRAHEDRON LETTERS, 1985, 26 (25) : 3049 - 3052
  • [45] SYNTHESIS AND NUCLEOPHILIC RING-OPENING REACTIONS OF ACTIVATED BICYCLO-[3.1.0]HEXANES
    KONDO, K
    HIRO, E
    TUNEMOTO, D
    TETRAHEDRON LETTERS, 1976, (49) : 4489 - 4492
  • [46] 1-AMINOADAMANTANE AS AGENT IN NUCLEOPHILIC-SUBSTITUTION, ADDITION AND RING-OPENING
    KREUTZBERGER, A
    SCHRODERS, HH
    TETRAHEDRON, 1976, 32 (09) : 1073 - 1074
  • [47] NUCLEOPHILIC RING-OPENING OF EPOXIDES BY ORGANOLITHIUM COMPOUNDS - AB-INITIO MECHANISMS
    HARDER, S
    VANLENTHE, JH
    HOMMES, NJRV
    SCHLEYER, PV
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2508 - 2514
  • [48] Nucleophilic substitution and electron transfer in the ring-opening reactions of β-lactones:: A short review
    Jedlinski, Z
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) : 1249 - 1254
  • [49] Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
    Zhang, Wuyuan
    Li, Huanhuan
    Younes, Sabry H. H.
    de Santos, Patricia Gomez
    Tieves, Florian
    Grogan, Gideon
    Pabst, Martin
    Alcalde, Miguel
    Whitwood, Adrian C.
    Hollmann, Frank
    ACS CATALYSIS, 2021, 11 (05): : 2644 - 2649
  • [50] Synthesis of R- and S-MDMA via nucleophilic ring-opening of homochiral N-tosylaziridines
    Lewis, Katie D.
    Pullella, Glenn A.
    Loh, Han Chern
    Skelton, Brian W.
    Flematti, Gavin R.
    Piggott, Matthew J.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2023, 76 (05) : 299 - 310
12345