PHOTOINDUCED ELECTRON-TRANSFER REACTION OF 7-BENZHYDRYLIDENENORBORNENE - CHEMICAL CAPTURE OF A RADICAL CATION INTERMEDIATE WITH NONCLASSICAL CATION CHARACTER

被引:14
作者
HIRANO, T [1 ]
SHIINA, S [1 ]
OHASHI, M [1 ]
机构
[1] UNIV ELECTROCOMMUN,DEPT APPL PHYS & CHEM,CHOFU,TOKYO 182,JAPAN
关键词
D O I
10.1039/c39920001544
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A photoinduced electron-transfer reaction of benzhydrylidenenorbornene 1 as an electron donor gives the radical cation 1+., which could be captured chemically by methanol or by the intramolecular hydroxy group, indicating the existence of a strong homoconjugative interaction between the exocyclic double bond and the C(2)-C(3) double bond.
引用
收藏
页码:1544 / 1545
页数:2
相关论文
共 17 条
[1]   ELECTRON-TRANSFER REACTIONS OF BICYCLO[4.2.1]NONATRIENES - FORMATION OF A BISHOMOHEPTAFULVENE RADICAL CATION [J].
ABELT, CJ ;
ROTH, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6734-6739
[2]   RADICAL IONS IN PHOTOCHEMISTRY .3. PHOTOSENSITIZED (ELECTRON-TRANSFER) CLEAVAGE OF BETA-PHENETHYL ETHERS [J].
ARNOLD, DR ;
MAROULIS, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (19) :5931-5936
[3]   THE 7-NORBORNADIENYL CATION - AN NMR/IGLO VALIDATION OF ITS AB-INITIO STRUCTURE [J].
BREMER, M ;
SCHOTZ, K ;
SCHLEYER, PV ;
FLEISCHER, U ;
SCHINDLER, M ;
KUTZELNIGG, W ;
KOCH, W ;
PULAY, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (08) :1042-1044
[4]   APPLICATIONS OF PHOTOELECTRON-SPECTROSCOPY .34. PI-ORBITAL SEQUENCE IN NORBORNADIENE AND RELATED HYDROCARBONS [J].
HEILBRONNER, E ;
MARTIN, HD .
HELVETICA CHIMICA ACTA, 1972, 55 (05) :1490-+
[5]   BICYCLOFULVENES .2. C-13-NMR SPECTROSCOPIC INVESTIGATION OF POLARITY OF 1,1-DISUBSTITUTED OLEFINS [J].
HOFFMANN, RW ;
KURZ, H .
CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (01) :119-127
[6]   EXPERIMENTAL AND THEORETICAL-STUDIES ON THE HOMOCONJUGATION IN BICYCLIC CARBENIUM AND OXONIUM IONS IN THE GAS-PHASE [J].
HOURIET, R ;
SCHWITZGUEBEL, T ;
CARRUPT, PA ;
VOGEL, P .
TETRAHEDRON LETTERS, 1986, 27 (01) :37-40
[8]  
LUSTGARTEN RK, 1970, TETRAHEDRON LETT, P1699
[9]   REDOX-PHOTOSENSITIZED REACTIONS .7. AROMATIC HYDROCARBON-PHOTOSENSITIZED ELECTRON-TRANSFER REACTIONS OF FURAN, METHYLATED FURANS, 1,1-DIPHENYLETHYLENE, AND INDENE WITH P-DICYANOBENZENE [J].
MAJIMA, T ;
PAC, C ;
NAKASONE, A ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4499-4508
[10]   PHOTOCHEMICAL ELECTRON-TRANSFER REACTIONS OF 1,1-DIARYLETHYLENES [J].
MATTES, SL ;
FARID, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7356-7361