1,4-DIPHENYLBUTADIYNE

Chemical Properties

white crystalline needles

Uses

1,4-Diphenylbutadiyne was used in the preparation of 7,8-dehydropurpurin dimers via two-fold Pd-catalyzed [3+2] annulation of meso-bromoporphyrin.

Definition

ChEBI: 1,4-diphenylbutadiyne is an arylacetylene and a member of benzenes. It has a role as a fluorochrome.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 443, 1987 DOI: 10.1021/jo00379a025
Synthetic Communications, 20, p. 2181, 1990 DOI: 10.1080/00397919008053156
Tetrahedron Letters, 26, p. 523, 1985 DOI: 10.1016/S0040-4039(00)61928-7

General Description

1,4-Diphenylbutadiyne reacts with [WI₂(CO)₃(NCMe)₂] in CH₂Cl₂ to give the iodo-bridged dimer [W(μ-I)I(CO)(NCMe)(η²PhC₂C₂Ph)]₂. 1,4-Diphenylbutadiyne on UV irradiation with olefins such as 2,3-dimethyl-2-butene, 1,4-cyclohexadiene and dimethyl fumarate yields cross-cycloaddition products.