The Pyrolyses of 1,1,4,4-Tetraphenyl-1,4-butanediol and 1,1,4,4-Tetraphenyl-2-butene-1,4-diol Derivatives. Decomposition Reactions to Form Olefins via the Elimination of Two Mole Equivalents of the Hydroxydiphenylmethyl Radical

Article abstract of DOI:10.1246/bcsj.58.3118

The pyrolysis of 1,1,2,4,4-pentaphenyl-1,4-butandiol, trans-1,2-bis(hydroxydiphenylmethyl)hexane, trans-1,2-bis(hydroxydiphenylmethyl)indan, and cis-endo- and trans-1,2-bis(hydroxydiphenylmethyl)bicyclo<2.2.1>heptane gave styrene, cyclohexene, indene, and norbornene respectively, accompanied by benzophenone and benzhydrol.The pyrolysis of trans-1,2-bis(hydroxydiphenylmethyl)spiro<2.6>nona-4,6,8-triene afforded indene via rearrangement to form trans-1,2-bis(hydroxydiphenylmethyl)indan.The pyrolysis of cis-1,1,4,4-tetraphenyl-2-butene-1,4-diol afforded 2,2,5,5-tetraphenyl-2,5-dihydrofuran.On the other hand, trans-1,1,4,4-tetraphenyl-2- butene-1,4-diol afforded 1,2,4,4-tetraphenyl-3-buten-1-one.The mechanisms of these decomposition reactions are discussed.