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
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
  • [31] A FURTHER STUDY OF THE COURSE OF RING-OPENING OF UNSYMMETRICAL EPOXIDES WITH NUCLEOPHILIC REAGENTS
    ZUIDEMA, GD
    COOK, PL
    VANZYL, G
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (02) : 294 - 296
  • [32] NUCLEOPHILIC RING-OPENING ADDITIONS TO 1,1-DISUBSTITUTED CYCLOPROPANES
    STEWART, JM
    WESTBERG, HH
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06): : 1951 - &
  • [33] Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst
    Sun, Hongnan
    Yang, Chao
    Lin, Run
    Xia, Wujiong
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2775 - 2780
  • [34] REGIOSELECTIVE NUCLEOPHILIC RING-OPENING OF 2,3-AZIRIDINO ALCOHOLS
    TANNER, D
    HE, HM
    SOMFAI, P
    TETRAHEDRON, 1992, 48 (29) : 6069 - 6078
  • [35] NUCLEOPHILIC RING-OPENING OF BRIDGING THIETANES IN OPEN TRIOSMIUM CLUSTER COMPLEXES
    ADAMS, RD
    BELINSKI, JA
    ORGANOMETALLICS, 1992, 11 (07) : 2488 - 2493
  • [36] The vicarious nucleophilic substitution of hydrogen proceeding via a cyclopropane ring-opening
    Stalewski, J
    TETRAHEDRON LETTERS, 1998, 39 (51) : 9523 - 9526
  • [37] Scalable Preparation of Synthetic Mucins via Nucleophilic Ring-Opening Polymerization of Glycosylated N-Carboxyanhydrides
    Lema, Manuel A.
    Nava-Medina, Ilse B.
    Cerullo, Antonio R.
    Abdelaziz, Radwa
    Jimenez, Stephanie M.
    Geldner, Jacob B.
    Abdelhamid, Mohamed
    Kwan, Chak-Shing
    Kharlamb, Lily
    Neary, Michelle C.
    Braunschweig, Adam B.
    MACROMOLECULES, 2022, 55 (11) : 4710 - 4720
  • [38] Synthesis of primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines
    Gajda, T
    Napieraj, A
    OsowskaPacewicka, K
    Zawadzki, S
    Zwierzak, A
    TETRAHEDRON, 1997, 53 (13) : 4935 - 4946
  • [39] A NEW NUCLEOPHILIC RING-OPENING OF AN ACTIVATED CYCLOPROPANE AND A FORMAL SYNTHESIS OF(+/-)-CARBOVIR
    TANIMORI, SJ
    TSUBOTA, M
    HE, MQ
    NAKAYAMA, M
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (11) : 2091 - 2093
  • [40] REGIOSPECIFICITY IN THE NUCLEOPHILIC RING-OPENING REACTIONS OF GEM-DICHLOROCYCLOPROPYLCARBINYL CATIONS
    DEWEESE, FT
    MINTER, DE
    NOSOVITCH, JT
    RUDEL, MG
    TETRAHEDRON, 1986, 42 (01) : 239 - 244