TRANSMISSION OF ELECTRONIC EFFECTS THROUGH 2-[DONOR]-1-[ACCEPTOR]-CYCLOPROPANE

被引:3
作者
ALONSO, ME [1 ]
PEKERAR, SV [1 ]
BORGO, ML [1 ]
机构
[1] INST VENEZOLANO INVEST CIENT, CTR QUIM, CARACAS 1010A, VENEZUELA
关键词
!sup]13[!/sup]C NMR; !sup]1[!/sup]H NMR; Cyclopropane; Through‐the‐ring conjugation;
D O I
10.1002/mrc.1260281110
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The through‐ring conjugation between π‐donor and attractor substitutents on vicinal carbons of cyclopropane with the direct participation of the ring was assessed using proton and 13C NMR. Appropriate 1H NMR correlations were obtained between σp and δH of the trimethylene protons. However, aryl through‐space field effects were found to obscure individual conjugative effects. Conversely, the 13C NMR data implied the occurrence of competitive conjugation of π‐groups with the ring but gave no proof for the existence of the actual transmission of conjugative effects through the C‐1–C‐2 bond of the ring. Copyright © 1990 John Wiley & Sons, Ltd.
引用
收藏
页码:956 / 962
页数:7
相关论文
共 42 条
[1]   TRANSMISSION OF ELECTRONIC SUBSTITUENT EFFECTS IN 4-SUBSTITUTED BICYCLO[2.2.2]OCTYL SYSTEMS [J].
ADCOCK, W ;
BUTT, G ;
KOK, GB ;
MARRIOTT, S ;
TOPSOM, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2551-2557
[2]  
ALONSO ME, 1980, J ORG CHEM, V45, P5430
[3]  
BACH RD, 1979, J AM CHEM SOC, V46, P101
[4]  
BARTELL LS, 1965, J CHEM PHYS, V43, P647, DOI 10.1063/1.1696787
[5]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .10. SOLVOLYSIS OF "1-(P-CYCLOPROPYLPHENYL)-1-ARYLETHYL AND 1-(P-ISOPROPYLPHENYL)-1-ARYLETHYL CHLORIDES - TEST OF TOOL OF INCREASING ELECTRON DEMAND TO SYSTEMS WITH RELATIVELY SMALL ELECTRONIC RESPONSE [J].
BROWN, HC ;
RAVINDRANATHAN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (10) :2895-2898
[6]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .16. EFFECT OF CONFORMATION OF CYCLOPROPYL, PHENYL, AND ISOPROPYL SUBSTITUENTS ON THEIR ELECTRONIC CONTRIBUTIONS TO ELECTRON-DEFICIENT CENTER [J].
BROWN, HC ;
CLEVELAND, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1792-1799
[7]   THE ABSORPTION SPECTRA OF SOME DERIVATIVES OF CYCLOPROPANE. [J].
Carr, Emma P. ;
Bury, C. Pauline .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1918, 40 :1590-1600
[8]   RELATIVE CONJUGATIVE ABILITIES OF 3-MEMBERED RING HETEROCYCLES WITH BENZENE BASED ON C-13 AND N-15 NMR [J].
CRIST, DR ;
JORDAN, GJ ;
MOORE, DW ;
HASHMALL, JA ;
BORSETTI, AP ;
TURUJMAN, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4136-4142
[9]   13CNMR STUDIES .V. CARBON-13 SPECTRA OF SOME SUBSTITUTED STYRENES [J].
DHAMI, KS ;
STOTHERS, JB .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (02) :510-&
[10]  
DOYLE MP, 1987, CHEM REV, V87, P411