Stereochemical outcome of McMurry coupling

Rusli Daik, W. James Feast, Andrei S. Batsanov, Judith A K Howard

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

McMurry coupling of 4-bromoacetophenone using the product of reaction of lithium aluminium hydride and titanium trichloride in THF gives 2,3-bis(4-bromophenyl)-2-butenes in a cis : trans ratio of approximately 9 : 1. This unexpected result was confirmed by X-ray crystallography and resolves an inconsistency in earlier literature assignments. Coupling of 4-bromobenzophenone under the same conditions gives cis and trans isomers in an approximately 1 : 1 ratio.

Original languageEnglish
Pages (from-to)1047-1049
Number of pages3
JournalNew Journal of Chemistry
Volume22
Issue number10
Publication statusPublished - Oct 1998
Externally publishedYes

Fingerprint

X ray crystallography
Butenes
Hydrides
Isomers
Lithium
Titanium
Aluminum
2-butene
lithium aluminum hydride
4-bromoacetophenone
titanium trichloride

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Daik, R., Feast, W. J., Batsanov, A. S., & Howard, J. A. K. (1998). Stereochemical outcome of McMurry coupling. New Journal of Chemistry, 22(10), 1047-1049.

Stereochemical outcome of McMurry coupling. / Daik, Rusli; Feast, W. James; Batsanov, Andrei S.; Howard, Judith A K.

In: New Journal of Chemistry, Vol. 22, No. 10, 10.1998, p. 1047-1049.

Research output: Contribution to journalArticle

Daik, R, Feast, WJ, Batsanov, AS & Howard, JAK 1998, 'Stereochemical outcome of McMurry coupling', New Journal of Chemistry, vol. 22, no. 10, pp. 1047-1049.
Daik R, Feast WJ, Batsanov AS, Howard JAK. Stereochemical outcome of McMurry coupling. New Journal of Chemistry. 1998 Oct;22(10):1047-1049.
Daik, Rusli ; Feast, W. James ; Batsanov, Andrei S. ; Howard, Judith A K. / Stereochemical outcome of McMurry coupling. In: New Journal of Chemistry. 1998 ; Vol. 22, No. 10. pp. 1047-1049.
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