A NEW MODE FOR THE GENERATION OF O-XYLYLENE BY PERI-SELENIUM PARTICIPATION FROM 8,13-DIHYDROBENZO[G]NAPHTHO[1,8-BC][1,5]DISELENONIN UNDER IRRADIATION

被引:28
作者
FUJIHARA, H
YABE, M
FURUKAWA, N
机构
[1] Department of Chemistry, University of Tsukuba, Tsukuba
关键词
D O I
10.1021/jo00072a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new cyclic bis-selenide containing benzylic methylene groups and a naphthalene ring, 8,13-dihydrobenzo[g]naphtho[1,8-bc] [1,5]diselenonin (1), was stable in the dark; however, the C-Se bond of 1 was readily cleaved to form o-xylylene (2) and naphtho[1,8-cd]-1,2-diselenole (3) under the scattered light in the laboratory. The o-xylylene generated from 1 under the scattered light or UV irradiation (254 nm) was trapped by several dienophiles.
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页码:5291 / 5292
页数:2
相关论文
共 16 条
[1]   PI,PI-BIRADICALOID HYDROCARBONS - ORTHO-XYLYLENE - PHOTOCHEMICAL PREPARATION FROM 1,4-DIHYDROPHTHALAZINE IN RIGID GLASS, ELECTRONIC SPECTROSCOPY, AND CALCULATIONS [J].
FLYNN, CR ;
MICHL, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (10) :3280-3288
[2]   HYPERVALENT SELENURANE WITH THE CHALCOGENIUM CATION (SE+, S+) FROM 1,11-(METHANOSELENOMETHANO)-5H,7H-DIBENZO[B,G][1,5]DISELENOCIN AND ITS SULFUR DERIVATIVE - INTERCONVERTIBLE REDOX STRUCTURES BY MULTICENTER CHALCOGENIDE PARTICIPATION [J].
FUJIHARA, H ;
MIMA, H ;
ERATA, T ;
FURUKAWA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3117-3118
[3]   A NEW OXIDATIVE SE-DEALKYLATION IN SELENO-PUMMERER REACTION OF 1,8-BIS(METHYLSELENO)NAPHTHALENE AND NAPHTHO[1,8-B,C]-1,5-DISELENOCIN INDUCED BY PERI-SELENIUM PARTICIPATION [J].
FUJIHARA, H ;
SAITO, R ;
YABE, M ;
FURUKAWA, N .
CHEMISTRY LETTERS, 1992, (08) :1437-1440
[4]   1,5-DISELENACYCLO-OCTANE - SYNTHESIS AND THE 1ST ISOLATION OF THE DISELENIDE PF6-SALT [R2SE+-SE+R2] [J].
FUJIHARA, H ;
AKAISHI, R ;
ERATA, T ;
FURUKAWA, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1789-1790
[5]   THERMAL, PHOTOCHEMICAL, AND TRANSITION-METAL MEDIATED ROUTES TO STEROIDS BY INTRAMOLECULAR DIELS-ALDER REACTIONS OF ORTHO-XYLYLENES (ORTHO-QUINODIMETHANES) [J].
FUNK, RL ;
VOLLHARDT, KPC .
CHEMICAL SOCIETY REVIEWS, 1980, 9 (01) :41-61
[6]   FLASH PYROLYSIS OF SELENIDES - SYNTHESES OF BIBENZYLS, OLEFINS, AND RELATED-COMPOUNDS [J].
HIGUCHI, H ;
OTSUBO, T ;
OGURA, F ;
YAMAGUCHI, H ;
SAKATA, Y ;
MISUMI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (01) :182-187
[7]   EFFICIENT AND VERSATILE GENERATION OF ORTHO-XYLYLENES BY FLUORIDE ANION INDUCED 1,4 ELIMINATION OF ORTHO-(ALPHA-TRIMETHYLSILYLALKYL)BENZYLTRIMETHYLAMMONIUM HALIDES [J].
ITO, Y ;
NAKATSUKA, M ;
SAEGUSA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :863-865
[8]   ORTHO-QUINODIMETHANE GENERATION FROM ALPHA,ALPHA'-DIHALO-ORTHO-XYLENES BY USE OF SODIUM BENZENETELLUROLATE [J].
KAMBE, N ;
TSUKAMOTO, T ;
MIYOSHI, N ;
MURAI, S ;
SONODA, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (10) :3013-3018
[9]   ORTHO-XYLYLENES AND ISOINDENES AS REACTION INTERMEDIATES [J].
MCCULLOUGH, JJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (08) :270-276
[10]  
OPPOLZER W, 1978, SYNTHESIS-STUTTGART, P793