CONFORMATIONAL EFFECTS IN PHOTOCYCLIZATION OF 6-MEMBERED AND 7-MEMBERED RING ALKOXYKETONES

被引:17
作者
HORAGUCHI, T
IWANAMI, H
TANAKA, T
HASEGAWA, E
SHIMIZU, T
机构
关键词
D O I
10.1039/c39910000044
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Irradiation of 8-alkoxytetrahydro-1-napthalenones 5 gave rearranged naphthyl alcohols 11 as major products and in contrast, 4-alkoxytetrahydrobenzocyclohepten-5-ones 6 afforded tetrahydrocyclohepta[cd]benzofurans 14 in good yields; the difference in reactivities is attributed to the conformation of six- and seven-membered rings.
引用
收藏
页码:44 / 46
页数:3
相关论文
共 16 条
[1]   O-17 NMR-STUDIES OF TORSION ANGLE RELATIONSHIPS IN ARYL ALKYL KETONES AND AROMATIC-ALDEHYDES [J].
BOYKIN, DW ;
BALAKRISHNAN, P ;
BAUMSTARK, AL .
MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (03) :248-250
[2]   SYNTHESIS AND PHOTOCHEMISTRY OF 2,4,6-TRI-TERT-BUTYLACETOPHENONE [J].
DITTO, SR ;
CARD, RJ ;
DAVIS, PD ;
NECKERS, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :894-896
[3]   ULTRAVIOLET ABSORPTION SPECTRA OF HINDERED KETONES [J].
HEDDEN, GD ;
BROWN, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3744-3748
[4]   PHOTOLYSIS OF 2-(BENZYLOXY)-4-(DODECYLOXY)BENZOPHENONE AND 2-ISOPROPOXY-4-METHOXYBENZOPHENONE [J].
LAPPIN, GR ;
ZANNUCCI, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (13) :1808-&
[5]  
LAPPIN GR, 1969, J CHEM SOC CHEM COMM, P113
[6]   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
[7]   2-HYDROXY-4,6-DI-T-BUTYLBENZOPHENONE PHOTOREACTIVITY [J].
OCONNELL, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (23) :6550-&
[8]   HEAVY-ATOM EFFECTS ON STEREOCHEMISTRY OF PHOTOABSTRACTION-CYCLIZATION IN A CARBONYL SYSTEM [J].
PAPPAS, SP ;
ZEHR, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (25) :7112-&
[9]   PHOTOCYCLIZATION OF METHYL-O-BENZYLOXYPHENYLGLYOXYLATE [J].
PAPPAS, SP ;
PAPPAS, BC ;
BLACKWEL.JE .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) :3066-&
[10]  
PAPPAS SP, 1966, TETRAHEDRON LETT, P1171