Intrinsic pyramidal nitrogen of N-sulfonylamides

被引:36
作者
Ohwada, T
Okamoto, I
Shudo, K
Yamaguchi, K
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 113, Japan
[2] Chiba Univ, Ctr Chem Anal, Inage Ku, Chiba 263, Japan
关键词
D O I
10.1016/S0040-4039(98)01746-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The pyramidalization of the nitrogen in sulfonamides of 7-azabicyclo[2.2.1]heptane is enhanced in the solid state as compared with the corresponding monocyclic sulfonamides of pyrrolidine and 3-pyrroline. We postulate a general structural motif of pyramidal nitrogen in sulfonamides. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7877 / 7880
页数:4
相关论文
共 49 条
[1]   A SUBSTRATE FOR THE ASYMMETRIC NAZAROV CYCLIZATION [J].
ANDREWS, JFP ;
REGAN, AC ;
WALLIS, JD ;
POVEY, DC .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 :2196-2199
[2]   ELECTROPHILIC SUBSTITUTION AT SATURATED CARBON.31. EFFECTS OF ATTACHED SECOND-ROW ELEMENTS ON RATES OF NITROGEN INVERSION IN AZIRIDINES [J].
ANET, FAL ;
TREPKA, RD ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :357-&
[3]   SYNTHESIS OF N-BOC-3-AZABICYCLO[3.3.0]OCTAN-7-ONE VIA REDUCTIVE PAUSON-KHAND CYCLIZATION AND SUBSEQUENT CONVERSION TO A NOVEL DIAZATRICYCLIC RING-SYSTEM [J].
BECKER, DP ;
FLYNN, DL .
TETRAHEDRON, 1993, 49 (23) :5047-5054
[4]   A 3-PHENYLSULFINYL-1-PHENYLSULFONYLINDOLE [J].
BEDDOES, RL ;
KETTLE, JG ;
JOULE, JA .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1994, 50 :1989-1992
[5]   THE GEOMETRY AT NITROGEN IN N-PHENYLSULFONYL-PYRROLES AND N-PHENYLSULFONYL-INDOLES - THE GEOMETRY OF SULFONAMIDES [J].
BEDDOES, RL ;
DALTON, L ;
JOULE, JA ;
MILLS, OS ;
STREET, JD ;
WATT, CIF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (06) :787-797
[6]   ABINITIO CALCULATIONS ON N-METHYLMETHANESULFONAMIDE AND METHYL METHANESULFONATE FOR THE DEVELOPMENT OF FORCE-FIELD TORSIONAL PARAMETERS AND THEIR USE IN THE CONFORMATIONAL-ANALYSIS OF SOME NOVEL ESTROGENS [J].
BINDAL, RD ;
GOLAB, JT ;
KATZENELLENBOGEN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :7861-7868
[7]   The chiral S-N axis in sulfenamides: Enantiomeric resolution, direct demonstration of optical activity, and kinetics of interconversion [J].
Blanca, MBD ;
Maimon, E ;
Kost, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (20) :2216-2219
[8]  
CALCAGNI A, 1991, INT J PEPT PROT RES, V37, P167
[9]   RING-SIZE EFFECTS ON THE IONIZATION-POTENTIALS OF N-SUBSTITUTED AZACYCLOAKANES [J].
CAULETTI, C ;
DIVONA, ML ;
GARGANO, P ;
GRANDINETTI, F ;
GALLI, C ;
LILLOCCI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (05) :667-670
[10]   SYNTHESIS OF CARBAZOMYCIN-B [J].
CLIVE, DLJ ;
ETKIN, N ;
JOSEPH, T ;
LOWN, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2442-2445