THE NOVEL PHOTOCHEMICAL BEHAVIOR OF TRIPTYCENE-1,4-QUINONE

被引:9
作者
FU, TY [1 ]
GAMLIN, JN [1 ]
OLOVSSON, G [1 ]
SCHEFFER, JR [1 ]
TROTTER, J [1 ]
YOUNG, DT [1 ]
机构
[1] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER,BC V6T 1Z1,CANADA
关键词
D O I
10.1016/0040-4039(95)00228-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triptycene-1,4-quinone (1) reacts photochemically in solution to give different products depending on the solvent employed and on the presence or absence of oxygen. The structures of the photoproducts have been elucidated by spectroscopic methods, independent synthesis and single crystal X-ray diffractometry, and possible mechanistic pathways leading to their formation are presented and discussed. Unexpectedly, quinone 1 was found to be photochemically inert in the crystalline state. The X-ray crystal structure of 1 reveals the probable reason for this behavior.
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收藏
页码:2025 / 2028
页数:4
相关论文
共 10 条
[1]   CYCLOPROPANOL FORMATION VIA BETA-HYDROGEN ATOM ABSTRACTION - THE 5 MEMBERED TRANSITION-STATE ANALOG OF THE NORRISH TYPE-II REACTION [J].
ARIEL, S ;
ASKARI, SH ;
SCHEFFER, JR ;
TROTTER, J .
TETRAHEDRON LETTERS, 1986, 27 (07) :783-786
[2]   Triptycene (9,10-o-benzenoanthracene [J].
Bartlett, PD ;
Ryan, MJ ;
Cohen, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2649-2653
[3]   DIFFERENCES IN PHOTOCHEMICAL REACTIVITY OF 9,10-ETHENOANTHRACENE DERIVATIVES IN LIQUID AND CRYSTALLINE MEDIA [J].
CHEN, JX ;
SCHEFFER, JR ;
TROTTER, J .
TETRAHEDRON, 1992, 48 (16) :3251-3274
[4]   5,8-DIHYDROXY-9,10-DIHYDRO-9,10-[1,2]BENZENOANTHRACENE-1,4-DIONE - INTRA-MOLECULAR TRIPTYCENE QUINHYDRONE [J].
IWAMURA, H ;
MAKINO, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :720-721
[5]   EFFECTS OF SUBSTITUENTS AND SOLVENTS ON THE ELECTRONIC-SPECTRA OF 9,10-DIHYDRO-9,10-ORTHO-BENZENOANTHRACENE-1,4-DIONES - INTRAMOLECULAR CHARGE-TRANSFER [J].
KITAGUCHI, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (03) :800-807
[6]   PHOTOCHEMICAL HYDROGEN ABSTRACTION REACTIONS OF 9,10-DIHYDRO-9,10-ORTHO-BENZENOANTHRACENE-1,4-DIONE DERIVATIVES WITH XANTHENE - INTRAMOLECULAR CHARGE-TRANSFER QUENCHING [J].
KITAGUCHI, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) :3542-3548
[7]   SUBSTITUENT EFFECTS ON THE CHARGE-TRANSFER BAND SHIFTS IN 9,10-DIHYDRO-9,10-ORTHO-BENZENOANTHRACENE-1,4-DIONES - FURTHER CONFIRMATION OF THE CHARGE-TRANSFER TRANSITION FOR A SYMMETRY-FORBIDDEN CHARGE-TRANSFER INTERACTION [J].
YAMAMURA, K ;
NAKASUJI, K ;
MURATA, I ;
INAGAKI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (07) :396-397
[8]   EXPERIMENTAL AND THEORETICAL EXPLORATION OF THE DETAILED MECHANISM OF THE REARRANGEMENT OF BARRELENES TO SEMIBULLVALENES - DIRADICAL INTERMEDIATES AND TRANSITION-STATES [J].
ZIMMERMAN, HE ;
SULZBACH, HM ;
TOLLEFSON, MB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6548-6556
[9]  
ZIMMERMAN HE, 1991, ORGANIC PHOTOCHEMIST, V11, pCH1
[10]  
ZIMMERMAN HE, 1980, REARRANGEMENTS GROUN, pCH16