TANDEM CYCLIZATION OF ENYNYL AND DIYNYL ALKYLLITHIUMS

被引：7

作者：

BAILEY, WF ^{[1
]}

OVASKA, TV ^{[1
]}

机构：

[1] CONNECTICUT COLL, DEPT CHEM, NEW LONDON, CT 06320 USA

来源：

CHEMISTRY LETTERS | 1993年 / 05期

关键词：

D O I：

10.1246/cl.1993.819

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Undec-10-en-5-ynyllithium, generated from the corresponding iodide by low-temperature lithium - iodine exchange, undergoes two sequential 5-exo cyclizations when warmed to room temperature to afford 2-methyl-1-cyclopentylidenecyclopentane in 85% yield. Attempted tandem cyclization of an analogous diacetylenic alkyllithium was less successful.

引用

页码：819 / 820

页数：2

共 7 条

[1] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE
BAILEY, WF
PUNZALAN, ER
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5404 - 5406
[2] HIGHLY STEREOSELECTIVE TANDEM CYCLIZATIONS OF 5-HEXENYLLITHIUMS - PREPARATION OF ENDO-2-SUBSTITUTED BICYCLO[2.2.1]HEPTANES AND 3-SUBSTITUTED TRANS-BICYCLO[3.3.0]OCTANES
BAILEY, WF
KHANOLKAR, AD
GAVASKAR, KV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8053 - 8060
[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] PREPARATION AND FACILE CYCLIZATION OF 5-ALKYN-1-YLLITHIUMS
BAILEY, WF
OVASKA, TV
LEIPERT, TK
[J]. TETRAHEDRON LETTERS, 1989, 30 (30) : 3901 - 3904
[5] 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
[6] NORMANT JF, 1965, B SOC CHIM FR, P859
[7] STEREOSELECTIVE CYCLIC CARBOLITHIATION OF ALKYNE DERIVATIVES - A STEREOSELECTIVE SYNTHESIS OF EXOCYCLIC ALKENES
WU, GZ
CEDERBAUM, FE
NEGISHI, E
[J]. TETRAHEDRON LETTERS, 1990, 31 (04) : 493 - 496

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