KINETICS OF THE CYCLIZATION OF 5-HEXYN-1-YLLITHIUMS

被引：19

作者：

BAILEY, WF

OVASKA, TV

机构：

[1] Department of Chemistry, University of Connecticut, Storrs

来源：

ORGANOMETALLICS | 1990年 / 9卷 / 05期

关键词：

D O I：

10.1021/om00119a049

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The kinetics of the 5-exo-dig cyclization of 5-decyn-1-yllithium to (1-cyclopentylidenepent-1-yl)-lithium are characterized by ΔH = 23.0 ± 0.9 kcal/mol and ΔS* = +4.8 ± 3.3 eu (Ea = 23.6 ± 0.9 kcal/mol; In A = 32.9 ± 3.5). The phenyl-substituted analogue (6-phenyl-5-hexyn-1-yl)lithium cyclizes much more rapidly than the alkyl-substituted systems: k = (1.97 ± 0.08) X 10-3 at -50.6 °C (t1/2 = 6 min). © 1990, American Chemical Society. All rights reserved.

引用

页码：1694 / 1695

页数：2

共 11 条

[1] CYCLIZATION OF 5-HEXENYLLITHIUM TO (CYCLOPENTYLMETHYL)LITHIUM
BAILEY, WF
PATRICIA, JJ
DELGOBBO, VC
JARRET, RM
OKARMA, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) : 1999 - 2000
[2] PREPARATION AND REGIOSPECIFIC CYCLIZATION OF ALKENYLLITHIUMS
BAILEY, WF
NURMI, TT
PATRICIA, JJ
WANG, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) : 2442 - 2448
[3] TANDEM ANIONIC CYCLIZATION APPROACH TO POLYCARBOCYCLIC PRODUCTS
BAILEY, WF
ROSSI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 765 - 766
[4] REACTIONS OF 1-HALO-5-HEXENES WITH ALKYLLITHIUMS - EVIDENCE FOR A PRONOUNCED HALOGEN EFFECT ON THE MECHANISM OF THE METAL-HALOGEN INTERCHANGE REACTION OF PRIMARY ALKYL-HALIDES
BAILEY, WF
PATRICIA, JJ
NURMI, TT
[J]. TETRAHEDRON LETTERS, 1986, 27 (17) : 1865 - 1868
[5] METAL-HALOGEN INTERCHANGE BETWEEN TERT-BUTYLLITHIUM AND 1-IODO-5-HEXENES PROVIDES NO EVIDENCE FOR SINGLE-ELECTRON TRANSFER
BAILEY, WF
PATRICIA, JJ
NURMI, TT
WANG, W
[J]. TETRAHEDRON LETTERS, 1986, 27 (17) : 1861 - 1864
[6] PREPARATION AND FACILE CYCLIZATION OF 5-ALKYN-1-YLLITHIUMS
BAILEY, WF
OVASKA, TV
LEIPERT, TK
[J]. TETRAHEDRON LETTERS, 1989, 30 (30) : 3901 - 3904
[7] INTRAMOLECULAR ADDITION OF ALKYLLITHIUMS TO ACETYLENES - REGIOSPECIFIC 4-EXO-DIG, 5-EXO-DIG, AND 6-EXO-DIG CYCLIZATIONS
BAILEY, WF
OVASKA, TV
[J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 627 - 630
[8] CYCLIZATIONS OF OMEGA-ALKYNYL HALIDES BY CR(II) REDUCTION
CRANDALL, JK
MICHAELY, WJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) : 4244 - 4248
[9] HILL EA, 1975, J ORGANOMET CHEM, V91, P123, DOI 10.1016/S0022-328X(00)89630-8
[10] KOSSA WC, 1971, TETRAHEDRON LETT, P3455

← 1 2 →