title: Studies of the condensation of sulfones with ketones and aldehydes.
abstract: [reaction: see text] The condensation of ketones or aldehydes with sulfones was shown to give a variety of products. Condensation of 2-methylcyclohexanone with dimethyl sulfone using potassium t-butoxide as base gave useful yields of 1,2-dimethylenecyclohexane. Under the same conditions, cycloheptanone, 3-methyl-2-butanone, and 2-butanone were converted to dienes. Remarkably, these reaction conditions converted acetophenone into p-terphenyl (10%) and (E)-1,4-diphenyl-3-penten-1-one (44%). Propiophenone was converted to 2'-methyl-p-terphenyl (61%). Using alpha-tetralone produced 1-methynaphthalene and naphthalene. No reaction took place with beta-tetralone. Using diethyl sulfone with alpha-tetralone lead to pure naphthalene. Condensation of isobutyraldehyde and dimethyl sulfone using potassium t-butoxide gave isoprene in low yield. Using benzaldehyde and benzyl phenyl sulfone in N,N-dimethylacetamide gave 1,2-diphenyl-1-phenylsulfonylethylene, N,N-dimethylcinnamide, and a complex condensation product. Only 1,2-diphenyl-1-phenylsulfonylethylene was obtained when the solvent was THF.
authors.affiliation: Organic Consultants, Inc., 132 East Broadway, Suite 107, Eugene, Oregon 97401, USA.
authors.forename: Michael E
authors.initials: ME
authors.lastname: Garst
authors.forename: Lloyd J
authors.initials: LJ
authors.lastname: Dolby
authors.forename: Shervin
authors.initials: S
authors.lastname: Esfandiari
authors.forename: Rachel A
authors.initials: RA
authors.lastname: Okrent
authors.forename: Alfred A
authors.initials: AA
authors.lastname: Avey