Protium–deuterium exchange of styrenes in dilute acid at elevated temperatures Academic Article uri icon

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abstract

  • A modified high temperature – dilute acid method is used to synthesize phenylethene-2,2-d2 ("styrene-2,2-d2") (1b), 2-phenylpropene-1,1,3,3,3-d5 ("α-trideuteriomethylstyrene-2,2-d5") (2b), and E-1-phenylpropene-2-d ("trans-β-methylstyrene-2-d") (3b) from phenylethene ("styrene") (1a), 2-phenylpropene ("α-methylstyrene") (2a), and E-1-phenylpropene ("trans-β-methylstyrene") (3a), respectively. The deuteriated substitution product E-1,3-diphenyl-1-butene-2,4,4,4-d4 (4b) is also obtained from 1a. Labelled substitution products 1,3,3-tri-trideuteriomethyl-1-phenylindane-2,2-d11 (5b), 4-trideuteriomethyl-2,4-diphenyl-1-pentene-1,1,3,3,5,5,5-d10 (6b), and E-4-trideuteriomethyl-2,4-diphenyl-2-pentene-1,1,1,3,5,5,5-d10 (7b) are obtained from 2-phenylpropene.

publication date

  • September 1, 1988