A NEW PHOTOCHEMICAL-SYNTHESIS OF DIHYDROPYRAZOLES - NOVEL MODE OF PHOTOCYCLIZATION OF SOME 1-IMINOBUT-3-ENES DERIVATIVES

被引:5
作者
ARMESTO, D [1 ]
HORSPOOL, WM [1 ]
MANCHENO, MJ [1 ]
ORTIZ, MJ [1 ]
机构
[1] UNIV DUNDEE,DEPT CHEM,DUNDEE DD1 4HN,SCOTLAND
关键词
D O I
10.1039/c39930000721
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
While some hydrazine derivatives 3 of 2,2-dimethyl-4,4-diphenylbut-3-enal undergo both the aza-di-pi-methane (ADPM) rearrangement and a novel cyclization to afford dihydropyrazole derivatives 5 in varying yields, the tosylhydrazone derivative of 3,3-dimethyl-5,5-diphenylpent-4-en-2-one 7 gives exclusively an excellent yield of the corresponding dihydropyrazole 8, in a reaction that is proposed to involve an electron transfer process.
引用
收藏
页码:721 / 722
页数:2
相关论文
共 10 条
[1]   SUBSTITUTION EFFECTS ON THE AZA-DI-PI-METHANE REARRANGEMENT OF IMINES [J].
ARMESTO, D ;
HORSPOOL, WM ;
LANGA, F ;
PEREZOSSORIO, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (08) :1039-1042
[2]   THE AZA-DI-PI-METHANE REARRANGEMENT OF 1-ARYL-4,4-DIMETHYL-6,6-DIPHENYL-2-AZAHEXA-2,5-DIENES - THE INFLUENCE OF SUBSTITUENTS ON THE N-BENZYL GROUP [J].
ARMESTO, D ;
HORSPOOL, WM ;
LANGA, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (07) :903-906
[3]   EXTENSION OF THE AZA-DI-PI-METHANE REACTION TO STABLE DERIVATIVES - PHOTOCHEMICAL CYCLIZATION OF BETA,GAMMA-UNSATURATED OXIME ACETATES [J].
ARMESTO, D ;
HORSPOOL, WM ;
LANGA, F ;
RAMOS, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :223-228
[4]   THE AZA-DI-PI-METHANE REARRANGEMENT OF STABLE DERIVATIVES OF 2,2-DIMETHYL-4,4-DIPHENYLBUT-3-ENAL [J].
ARMESTO, D ;
HORSPOOL, WM ;
MANCHENO, MJ ;
ORTIZ, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2348-2349
[5]   INTRAMOLECULAR ELECTRON-TRANSFER IN THE NOVEL PHOTOREACTION OF SOME BETA,GAMMA-UNSATURATED OXIME BORON-TRIFLUORIDE COMPLEXES - A NEW SYNTHETIC PATH TO DIHYDROISOXAZOLES [J].
ARMESTO, D ;
BARNES, JC ;
HORSPOOL, WM ;
LANGA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) :123-125
[6]   STUDIES ON THE SCOPE OF THE AZA-DI-PI-METHANE REARRANGEMENT OF BETA,GAMMA-UNSATURATED IMINES [J].
ARMESTO, D ;
LANGA, F ;
MARTIN, JAF ;
PEREZOSSORIO, R ;
HORSPOOL, WM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04) :743-746
[7]   THE AZA-DI-PI-METHANE REARRANGEMENT OF O-ACETYL 2,2-DIMETHYL-4,4-DIPHENYLBUT-3-ENAL OXIME [J].
ARMESTO, D ;
HORSPOOL, WM ;
LANGA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (24) :1874-1875
[8]  
ARMESTO D, 1986, J CHEM RES-S, P46
[9]   CHEMICALLY EFFICIENT AZA-DI-PI-METHANE PHOTOREACTIVITY WITH NOVEL STABLE DERIVATIVES OF BETA,GAMMA-UNSATURATED CARBONYL-COMPOUNDS [J].
ARMESTO, D ;
HORSPOOL, WM ;
MANCHENO, MJ ;
ORTIZ, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18) :2325-2329
[10]   WHY IS TRIFLUOROACETIC-ACID SUCH AN EFFECTIVE ONE-ELECTRON OXIDANT [J].
EBERSON, L ;
RADNER, F .
ACTA CHEMICA SCANDINAVICA, 1991, 45 (10) :1093-1095