SYNTHETIC PHOTOCHEMISTRY .60. ONE-POT FORMATION OF SPIROCYCLIC 3-ACETYL-2-HYDROXY-2-CYCLOPENTENONE DERIVATIVES FROM METHYLENECYCLOALKANES AND METHYL 2,4-DIOXOPENTANOATE

被引:5
作者
HATSUI, T
IKEDA, S
TAKESHITA, H
机构
[1] KYUSHU UNIV, INST ADV MAT STUDY 86, KASUGA KOEN, KASUGA, FUKUOKA 816, JAPAN
[2] KYUSHU UNIV, GRAD SCH ENGN SCI, KASUGA, FUKUOKA 816, JAPAN
关键词
D O I
10.1246/bcsj.66.870
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of proto-photocycloadducts of methyl 2,4-dioxopentanoate to methylenecycloalkanes and -alkenes spontaneously caused retro-benzilic acid rearrangement in high yields. The results are utterly different from those of sterically-crowded acyclic alkenes, with which the rearrangement occurred by thermolysis as a minor process.
引用
收藏
页码:870 / 876
页数:7
相关论文
共 16 条
[1]   PHOTOCHEMICAL SYNTHESES .6. FORMATION OF HEPTANDIONES FROM ACETYLACETONE AND ALKENES [J].
MAYO, PD ;
TAKESHITA, H .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1963, 41 (02) :440-&
[2]   SYNTHESIS OF OXOISODEHYDROLEUCODIN - A NOVEL GUAIANOLIDE FROM MONTANOA-IMBRICATA [J].
GREENE, AE ;
EDGAR, MT .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1468-1470
[3]   SYNTHETIC PHOTOCHEMISTRY .51. STRUCTURE ELUCIDATION OF THE PYROLYSATES FORMED BY RETRO-BENZILIC ACID REARRANGEMENT OF THE PROTO-PHOTOCYCLOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE-OLEFINS [J].
HATSUI, T ;
NOJIMA, C ;
TAKESHITA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (09) :2932-2938
[4]   ONE-POT FORMATION OF FUNCTIONALIZED CYCLOPENTENONE DERIVATIVES VIA RETRO-BENZILIC ACID REARRANGEMENT OF THE PROTO-PHOTOCYCLOADDUCTS OF METHYL 2,4-DIOXOPENTANOATE TO METHYLENECYCLOALKANES [J].
HATSUI, T ;
IKEDA, S ;
TAKESHITA, H .
CHEMISTRY LETTERS, 1992, (10) :1891-1894
[5]   SYNTHETIC PHOTOCHEMISTRY .54. THE PHOTOADDITION REACTION OF METHYL 2,4-DIOXOPENTANOATE WITH 2,5-DIMETHYL-2,4-HEXADIENE, A STERICALLY CROWDED CONJUGATED DIENE [J].
HATSUI, T ;
NOJIMA, C ;
TAKESHITA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (06) :1611-1616
[6]  
HATSUI T, 1991, CHEM EXPRESS, V6, P845
[7]  
HATSUI T, 1989, KYUSHU DAIGAKU SOGO, V11, P291
[8]  
JACKMAN LM, 1969, APPLICATIONS NUCLEAR, P84
[9]   SYNTHETIC PHOTOCHEMISTRY .50. ISOLATION AND THE X-RAY STRUCTURE DETERMINATION OF PHOTOCYCLODIMERS FORMED BY UV-LIGHT IRRADIATION OF ALKYL 2,4-DIOXOPENTANOATES [J].
MORI, A ;
NISHIYAMA, N ;
KOHGUCHI, Y ;
SHINKA, H ;
TAKESHITA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (05) :1666-1667
[10]   PHOTOCHEMICAL REARRANGEMENTS OF QUINONE MONOKETALS - SYNTHESIS OF SUBSTITUTED CYCLOPENTENONES [J].
PIRRUNG, MC ;
NUNN, DS .
TETRAHEDRON LETTERS, 1988, 29 (02) :163-166