The reactions of trifluoromethyl and trichloromethyl radicals with conjugated and methylene-interrupted dienes and enynes

El Soueni*, John M. Tedder, John C. Walton

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The photochemical addition of CF3I to buta-1,3-diene and vinylacetylene in the gas phase gave 1,4-adducts as the main products. In gas phase reactions only products derived from hydrogen abstraction were detected in the CF3I/penta-1,3-diene system, but the 1,4-adducts again predominated in the liquid phase. CCl3Br similarly gave a mixture of 1,2- and 1,4-adducts, the latter predominating, on photochemical reaction with penta-1,3-diene. The 1,2-adduct was the main product from the CCl3Br/pent-1-en-4-yn reaction, but some hydrogen abstraction was observed. The preference shown by conjugated dienes to give 1,4-adducts in the trans- configuration is interpreted in terms of steric factors and the propensity of dienes to adopt the s-trans conformation.

Original languageEnglish
Pages (from-to)51-63
Number of pages13
JournalJournal of Fluorine Chemistry
Volume17
Issue number1
DOIs
Publication statusPublished - 1 Jan 1981

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