SYNTHESIS OF NOVEL CAGE QUATERNARY-SALTS VIA NUCLEOPHILIC-SUBSTITUTION OF 1,3-DIIODOBICYCLO[1.1.1]PENTANE - FURTHER EVIDENCE FOR A STABLE 3-IODO-1-BICYCLO[1.1.1]PENTYL CATION

被引：8

作者：

ADCOCK, JL

GAKH, AA

机构：

[1] Department of Chemistry, The University of Tennessee, Knoxville

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)61221-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic substitution of 1,3-diiodobicyclo[1.1.1]pentane by tertiary amines and pyridines was investigated. The structure of cage quaternary salts obtained together with the observation of the competitive addition of pyridine in the reaction of [1.1.1]propellane with iodine indicate the existence of a relatively stable "hot intermediate" very close in its structure to a stabilized 3-iodo-1-bicyclo[1.1.1]pentyl cation.

引用

页码：4875 / 4878

页数：4

共 16 条

[1] ADCOCK JL, 1992, IN PRESS J AM CHEM S
[2] POLAR SUBSTITUENT EFFECTS IN 1,3-DISUBSTITUTED BICYCLO[1.1.1]PENTANES
APPLEQUIST, DE
RENKEN, TL
WHEELER, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) : 4985 - 4995
[3] CHANDRASEKHAR J, 1978, TETRAHEDRON LETT, P3393
[4] DELLA EW, 1989, J CHEM RES-S, P172
[5] SYNTHESIS AND SOLVOLYSIS OF 1-BROMOBICYCLO[1.1.1]PENTANE
DELLA, EW
TAYLOR, DK
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (05) : 945 - 948
[6] APPLICATION OF SEMIEMPIRICAL MOLECULAR-ORBITAL THEORY TO CATIONIC INTERMEDIATES INVOLVED IN THE SOLVOLYSIS OF 1-HALOBICYCLO[N.1.1]ALKANES
DELLA, EW
GILL, PMW
SCHIESSER, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4354 - 4357
[7] REARRANGEMENTS OF BICYCLO[N.1.1]ALKYLIUM CATIONS
DELLA, EW
SCHLESSER, CH
[J]. TETRAHEDRON LETTERS, 1987, 28 (33) : 3869 - 3872
[8] Fort R. C., 1973, CARBONIUM IONS, VIV, P1783
[9] FORT RC, 1966, ADV ALICYCL CHEM, V1, P284
[10] THE C1-C3 BOND IN [1.1.1]PROPELLANE
JACKSON, JE
ALLEN, LC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) : 591 - 599

← 1 2 →