2H- And13C-labelling studies on skeletal reorganization of 1,6-enynes

Hiromi Nakai, Naoto Chatani

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

2H- and 13C-labelling studies on skeletal reorganization of 1,6-enynes having a terminal alkyne moiety have been performed with various catalysts. The products are 1-vinylcyclopentenes, but two possible isomers, type I and II products, can be formed. The formation of type I involves the cleavage of the original C-C double bonds and migration of the terminal alkene carbon atom to the terminus of the alkyne. On the other hand, the formation of type II involves a double cleavage of the C-C double bond and the C-C triple bond, which is an anomalous bond connection. The product ratio is affected by the nature of the catalyst used. Type II is obtained as a major isomer in the case of late transition metal halides. On the other hand, the type I product forms exclusively in the presence of a typical element halide, such as InCl3.

Original languageEnglish
Pages (from-to)1494-1495
Number of pages2
JournalChemistry Letters
Volume36
Issue number12
DOIs
Publication statusPublished - 2007 Dec 5
Externally publishedYes

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Alkynes
Isomers
Labeling
Metal halides
Catalysts
Alkenes
Transition metals
Carbon
Atoms

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

2H- And13C-labelling studies on skeletal reorganization of 1,6-enynes. / Nakai, Hiromi; Chatani, Naoto.

In: Chemistry Letters, Vol. 36, No. 12, 05.12.2007, p. 1494-1495.

Research output: Contribution to journalArticle

Nakai, Hiromi ; Chatani, Naoto. / 2H- And13C-labelling studies on skeletal reorganization of 1,6-enynes. In: Chemistry Letters. 2007 ; Vol. 36, No. 12. pp. 1494-1495.
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