ELECTRON-TRANSFER-INDUCED PHOTOCYCLIZATION REACTIONS OF ARENE IMINIUM SALT SYSTEMS - EFFECTS OF CATION DIRADICAL DEPROTONATION AND DESILYLATION ON THE NATURE AND EFFICIENCIES OF REACTION PATHWAYS FOLLOWED

被引:51
作者
LAN, AJY [1 ]
HEUCKEROTH, RO [1 ]
MARIANO, PS [1 ]
机构
[1] UNIV MARYLAND,DEPT CHEM,COLLEGE PK,MD 20742
关键词
D O I
10.1021/ja00243a029
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:2738 / 2745
页数:8
相关论文
共 22 条
[1]   SEQUENTIAL ELECTRON-TRANSFER DESILYLATION METHODS FOR DIRADICAL PHOTOGENERATION AS PART OF SYNTHETIC ROUTES FOR ERYTHRINA ALKALOID SYNTHESIS [J].
AHMEDSCHOFIELD, R ;
MARIANO, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5667-5677
[2]   ENAMIDES IN ORGANIC-SYNTHESIS .2. N-VINYL AS N-H PROTECTING GROUP - SYNTHESIS OF CYCLIC IMINES FROM N-VINYLLACTAMS AND ORGANOLITHIUM REAGENTS [J].
BIELAWSKI, J ;
BRANDANGE, S ;
LINDBLOM, L .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (01) :97-99
[3]   ARENE IMINIUM SALT ELECTRON-TRANSFER PHOTOCHEMISTRY - MECHANISTICALLY INTERESTING PHOTOADDITION PROCESSES [J].
BORG, RM ;
HEUCKEROTH, RO ;
LAN, AJY ;
QUILLEN, SL ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2728-2737
[4]   SEQUENTIAL ELECTRON-TRANSFER DESILYLATION PATHWAYS FOR C-VINYLAZOMETHINE YLIDE FORMATION IN THE PHOTOCHEMISTRY OF (1-(TRIETHYLSILYL)ALLYL)IMINIUM SALTS [J].
CHEN, SF ;
ULLRICH, JW ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6160-6162
[5]   MODEL STUDIES EXAMINING THE APPLICATION OF ALLYLIMINIUM SALT PHOTOSPIROCYCLIZATION METHODOLOGIES IN SYNTHETIC APPROACHES TO THE HARRINGTONINE ALKALOIDS [J].
CHIU, FT ;
ULLRICH, JW ;
MARIANO, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :228-236
[6]  
Colvin E. W., 1981, SILICON ORGANIC SYNT, P97
[7]  
FARID SM, UNPUB
[8]  
HO GO, 1985, TETRAHEDRON LETT, P5867
[9]   1,5,-ELECTROCYCLIZATIONS - AN IMPORTANT PRINCIPLE OF HETEROCYCLIC CHEMISTRY [J].
HUISGEN, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (12) :947-973
[10]   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