PHOTOCYCLIZATION OF BETA-OXOESTERS - LIMITING FACTORS FOR REMOTE HYDROGEN ABSTRACTION THROUGH A MEDIUM-SIZED CYCLIC TRANSITION-STATE

被引:7
作者
HASEGAWA, T [1 ]
HORIKOSHI, Y [1 ]
IWATA, S [1 ]
YOSHIOKA, M [1 ]
机构
[1] SAITAMA UNIV,DEPT CHEM,URAWA,SAITAMA 338,JAPAN
关键词
D O I
10.1039/c39910001617
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
On irradiation, the omega-phenylalkyl beta-oxoesters 1 undergo photocyclization via remote hydrogen abstraction through a cyclic transition state of at least nine atoms.
引用
收藏
页码:1617 / 1618
页数:2
相关论文
共 12 条
[1]   INTRAMOLECULAR HYDROGEN ABSTRACTION IN KETONE PHOTOCHEMISTRY - THE 1ST EXAMPLES OF ZETA-HYDROGEN ABSTRACTION [J].
CARLESS, HAJ ;
MWESIGYEKIBENDE, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1673-1674
[2]   PHOTOCHEMICAL EPSILON-HYDROGEN ABSTRACTION AS A ROUTE TO TETRAHYDROPYRAN-3-OLS [J].
CARLESS, HAJ ;
FEKARURHOBO, GK .
TETRAHEDRON LETTERS, 1984, 25 (51) :5943-5946
[3]   PHOTOCYCLIZATION OF (OMEGA-DIALKYLAMINO)ALKYL BETA-OXOESTERS VIA REMOTE HYDROGEN TRANSFER [J].
HASEGAWA, T ;
OGAWA, T ;
MIYATA, K ;
KARAKIZAWA, A ;
KOMIYAMA, M ;
NISHIZAWA, K ;
YOSHIOKA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :901-905
[4]   PHOTOREACTIONS OF 2-(DIALKYLAMINO)ETHYL ESTERS OF GAMMA-OXO ACIDS VIA REMOTE HYDROGEN TRANSFER - INFLUENCE OF THE STABILITY AND CONFORMATIONAL FLEXIBILITY OF THE BIRADICAL INTERMEDIATE ON ITS CHEMICAL BEHAVIOR [J].
HASEGAWA, T ;
MUKAI, K ;
MIZUKOSHI, K ;
YOSHIOKA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (11) :3348-3350
[5]   PHOTOCYCLIZATION OF ALPHA-[ORTHO-(BENZYLOXY)PHENYL]ACETOPHENONE - TRIPLET-STATE EPSILON-HYDROGEN ABSTRACTION [J].
MEADOR, MA ;
WAGNER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) :419-420
[6]   SYNTHESIS AND PHOTOCHEMISTRY OF SOME NEW PENTACYCLOUNDECAN-8-ONES - PROBES FOR HYDROGEN ABSTRACTION IN THE PI-PLANE [J].
SAUERS, RR ;
SCIMONE, A ;
SHAMS, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6084-6089
[7]   STEREOELECTRONIC REQUIREMENTS FOR TYPE 2 CLEAVAGE OF CIS- AND TRANS-4-T-BUTYLCYCLOHEXANONES [J].
TURRO, NJ ;
WEISS, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (08) :2185-+
[8]   TYPE-II PHOTOPROCESSES OF PHENYL KETONES - COMPETITIVE DELTA-HYDROGEN ABSTRACTION AND GEOMETRY OF INTRAMOLECULAR HYDROGEN-ATOM TRANSFERS [J].
WAGNER, PJ ;
ZEPP, RG ;
KELSO, PA ;
KEMPPAIN.AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7500-&
[9]   CONFORMATIONAL FLEXIBILITY AND PHOTOCHEMISTRY [J].
WAGNER, PJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (12) :461-467
[10]   TYPE-II PHOTOELIMINATION AND PHOTOCYCLIZATION OF KETONES [J].
WAGNER, PJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (05) :168-&