PHOTOLYSIS OF 2-AMINO-2'-AZIDOBIPHENYLS - FORMAL FORMATION OF INTERNALLY TRAPPED DIDEHYDROAZEPINES

被引:5
作者
MURATA, S [1 ]
TSUJI, H [1 ]
TOMIOKA, H [1 ]
机构
[1] MIE UNIV, FAC ENGN, CHEM DEPT MAT, TSU, MIE 514, JAPAN
关键词
D O I
10.1246/bcsj.67.895
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photolysis of 2-amino-2'-azidobiphenyls iii diethylamine gave 4,10-dihydroazepino[2,3-b]indoles (7), the structure of which corresponded to the didehydroazepines formally trapped with an internal amino group. However, the yields of 7 were considerably low, which was due to the significant intramolecular interaction of the photolytically generated nitrene with an amino group, to afford benzo[c]-cinnoline as a final product.
引用
收藏
页码:895 / 897
页数:3
相关论文
共 14 条
[1]   2-AZIDO-2'-NITRENOBIPHENYL [J].
BOYER, JH ;
MIKOL, GJ .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (13) :734-&
[2]   1-AZA-1,2,4,6-CYCLOHEPTATETRAENE [J].
CHAPMAN, OL ;
LEROUX, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :282-285
[3]   PHENYL NITRENE - FLASH PHOTOLYTIC INVESTIGATION OF REACTION WITH SECONDARY-AMINES [J].
DEGRAFF, BA ;
GILLESPI.DW ;
SUNDBERG, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7491-7496
[4]   RING ENLARGEMENT IN PHOTOLYSIS OF PHENYL AZIDE [J].
DOERING, WVE ;
ODUM, RA .
TETRAHEDRON, 1966, 22 (01) :81-&
[5]   DIDEHYDROAZEPINES FROM THE PHOTOLYSIS OF PHENYL AZIDE AND 3-SUBSTITUTED AND 4-SUBSTITUTED PHENYL AZIDES ISOLATED IN LOW-TEMPERATURE MATRICES [J].
DONNELLY, T ;
DUNKIN, IR ;
NORWOOD, DSD ;
PRENTICE, A ;
SHIELDS, CJ ;
THOMSON, PCP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (02) :307-310
[6]   NEIGHBOURING-GROUP PARTICIPATION IN PYROLYSIS OF ARYL AZIDES [J].
DYALL, LK ;
KEMP, JE .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1968, (09) :976-&
[7]   DIBENZO[D,F][1,2,3]TRIAZEPINE AND ATTEMPTED GENERATION OF 2,2'-DIDEHYDROBIPHENYL [J].
GAIT, SF ;
PEEK, ME ;
REES, CW ;
STORR, RC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (11) :1248-1260
[8]   INFRARED-SPECTRUM OF TRIPLET PHENYLNITRENE - ON THE ORIGIN OF DIDEHYDROAZEPINE IN LOW-TEMPERATURE MATRICES [J].
HAYES, JC ;
SHERIDAN, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5879-5881
[9]   3H-AZEPINES AND RELATED SYSTEMS .4. PREPARATION OF 3H-AZEPIN-2-ONES AND 6H-AZEPINO[2,1-B]QUINAZOLIN-12-ONES BY PHOTOINDUCED RING EXPANSIONS OF ARYL AZIDES [J].
LAMARA, K ;
SMALLEY, RK .
TETRAHEDRON, 1991, 47 (12-13) :2277-2290
[10]   PHOTOCHEMISTRY OF PHENYL AZIDE - THE ROLE OF SINGLET AND TRIPLET PHENYLNITRENE AS TRANSIENT INTERMEDIATES [J].
LEYVA, E ;
PLATZ, MS ;
PERSY, G ;
WIRZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (13) :3783-3790