STERIC ACCELERATION OF INTRAMOLECULAR OXIME AND HYDRAZONE CYCLOADDITIONS

被引:11
作者
BISHOP, JE
FLAXMAN, KA
ORLEK, BS
SAMMES, PG
WELLER, DJ
机构
[1] SMITHKLINE BEECHAM PHARMACEUT, DEPT MED CHEM, HARLOW CM19 5AD, ESSEX, ENGLAND
[2] BRUNEL UNIV, DEPT CHEM, MOLEC PROBES UNIT, UXBRIDGE UB8 3PH, MIDDX, ENGLAND
[3] WHITBREAD PLC, WHITBREAD TECH CTR, LUTON LU1 3ET, BEDS, ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 20期
关键词
D O I
10.1039/p19950002551
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selected Conformational constraints, achieved by the incorporation of ortho-substituents in 2-substituted 1-allyloxybenzenes, where the substituent is a 1,3-dipole or its tautomeric precursor, as in oximes, can be employed to accelerate the 1,3-dipolar cycloaddition process. Some evidence that hydrazones preferentially react with the alkene group by prior oxidation to the corresponding nitrilimine species is presented.
引用
收藏
页码:2551 / 2555
页数:5
相关论文
共 33 条
[1]   SOME PERTINENT ASPECTS OF MECHANISM AS DETERMINED WITH SMALL MOLECULES [J].
BRUICE, TC .
ANNUAL REVIEW OF BIOCHEMISTRY, 1976, 45 :331-373
[2]   CHEMISTRY OF ARYLHYDRAZONES [J].
BUCKINGHAM, J .
QUARTERLY REVIEWS, 1969, 23 (01) :37-+
[3]   TRANS-ANNULAR REACTIONS OF DIBENZO[A,D]CYCLOALKENES .1. SYNTHESIS OF DIBENZO[A,D]CYCLOOCTEN-6,12-IMINES AND "DIBENZO[A,D]CYCLOHEPTEN-5,10-IMINES [J].
CHRISTY, ME ;
ANDERSON, PS ;
BRITCHER, SF ;
COLTON, CD ;
EVANS, BE ;
REMY, DC ;
ENGELHARDT, EL .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3117-3127
[4]  
FUSCO R, 1975, CHIM IND-MILAN, V57, P16
[5]   INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS OF NITRILE IMINES BEARING AN ALKENYL SUBSTITUENT [J].
GARANTI, L ;
SALA, A ;
ZECCHI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (08) :1389-1392
[6]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .31. GENERATION OF NITRONES FROM OXIMES - BACKGROUND AND SCOPE OF THE TANDEM 1,2-PROTOTROPY-INTRAMOLECULAR CYCLOADDITION SEQUENCE [J].
GRIGG, R ;
HEANEY, F ;
MARKANDU, J ;
SURENDRAKUMAR, S ;
THORNTONPETT, M ;
WARNOCK, WJ .
TETRAHEDRON, 1991, 47 (24) :4007-4030
[7]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .2. OXIME CYCLO-ADDITIONS - FORMATION OF 2-1 ADDUCTS [J].
GRIGG, R ;
JORDAN, M ;
TANGTHONGKUM, A ;
EINSTEIN, FWB ;
JONES, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (01) :47-57
[8]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .13. PROTOTROPIC GENERATION OF AZOMETHINE IMINES FROM HYDRAZONES [J].
GRIGG, R ;
DOWLING, M ;
JORDAN, MW ;
SRIDHARAN, V .
TETRAHEDRON, 1987, 43 (24) :5873-5886
[9]   X=Y - ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .35. GENERATION OF NITRONES FROM OXIMES - CLASS-3 PROCESSES - TANDEM INTRAMOLECULAR MICHAEL ADDITION (1,3-AZAPROTIO CYCLOTRANSFER) - INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS [J].
GRIGG, R ;
MARKANDU, J ;
PERRIOR, T ;
SURENDRAKUMAR, S ;
WARNOCK, WJ .
TETRAHEDRON, 1992, 48 (33) :6929-6952
[10]  
GRUNDMAN C, 1970, CHEM NITRILE GROUP, P799