MEROSTABILIZATION OF BIRADICALOID INTERMEDIATES AS A FACTOR IN DETERMINING RATES AND REGIOSELECTIVITY IN [4 + 2] CYCLOADDITION REACTIONS OF REISSERT HYDROFLUOROBORATE SALTS WITH ALKENES AND ALKYNES

被引:21
作者
MCEWEN, WE [1 ]
HUANG, ICW [1 ]
MARIN, CPC [1 ]
MCCARTY, F [1 ]
SEGNINI, EM [1 ]
ZEPP, CM [1 ]
LUBINKOWSKI, JJ [1 ]
机构
[1] UNIV SIMON BOLIVAR,DEPT CHEM,CARACAS,VENEZUELA
关键词
D O I
10.1021/jo00137a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:3098 / 3105
页数:8
相关论文
共 52 条
[21]   BASIS AND LIMITATIONS OF REACTIVITY-SELECTIVITY PRINCIPLE [J].
GIESE, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (03) :125-136
[22]   BASE-CATALYZED AND ACID-CATALYZED CONDENSATION REACTIONS OF REISSERT COMPOUNDS WITH VINYLPYRIDINES [J].
GIRIDHAR, V ;
MCEWEN, WE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (01) :121-&
[23]   RE-STATEMENT OF CONCERTED-DIRADICAL MECHANISM FOR 1,3-DIPOLAR CYCLOADDITION REACTIONS [J].
HARCOURT, RD .
TETRAHEDRON, 1978, 34 (20) :3125-3127
[24]   CONCERTED NATURE OF 1,3-DIPOLAR CYCLOADDITIONS AND QUESTION OF DIRADICAL INTERMEDIATES [J].
HUISGEN, R .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (03) :403-419
[26]  
Huisgen R., 1963, ANGEW CHEM INT EDIT, P565, DOI [10.1002/anie.196305651, DOI 10.1002/ANIE.196305651]
[27]   CAPTODATIVE SUBSTITUENT EFFECTS AND THE CHROMOPHORIC SYSTEM OF INDIGO [J].
KLESSINGER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1980, 19 (11) :908-909
[28]   REACTION OF ACETYLENE WITH FULMINIC ACID - PROTOTYPE 1,3-DIPOLAR CYCLOADDITION [J].
KOMORNICKI, A ;
GODDARD, JD ;
SCHAEFER, HF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :1763-1769
[29]  
LIAO TK, 1966, J ORG CHEM, V31, P4110
[30]   CONDENSATION OF 2-BENZOYL-1,2-DIHYDROISOQUINALDONITRILE HYDROFLUOROBORATE WITH ETHYL CINNAMATE AND RELATED COMPOUNDS [J].
LING, CF ;
SANTELLA, RP ;
SHEN, YH ;
MCEWEN, WE .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :661-663