17351-16-5Relevant academic research and scientific papers
Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C 2-symmetrical 1,2-, 1,3- and 1,4-diols
Lemiègre, Lo?c,Lesetre, Fleur,Combret, Jean-Claude,Maddaluno, Jacques
, p. 415 - 427 (2007/10/03)
Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 α,β-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed.
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
Saito, Katsuhiro,Horie, Yoichi,Mukai, Toshio,Toda, Takashi
, p. 3118 - 3124 (2007/10/02)
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)bicycloheptane gave styrene, cyclohexene, indene, and norbornene respectively, accompanied by benzophenone and benzhydrol.The pyrolysis of trans-1,2-bis(hydroxydiphenylmethyl)spironona-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.
