80361-32-6Relevant academic research and scientific papers
Synthesis of cis-Jasmone via the Retroaldol-aldol Condensation of 3-(cis-3-hexenyl)-2-cyclopentenone in an Autoclave
Yoshida, Takashi,Saito, Shojiro
, p. 3931 - 3932 (2007/10/02)
cis-Jasmone was efficiently synthesized from 2-cyclopentenone.The treatment of cyclopentenone with sodium p-toluenesulfinate gave 3-(p-tolylsulfonyl)cyclopentanone in a 92.5percent yield.The alkylation of the sulfone, after the protection of the ketone, with cis-1-bromo-3-hexene, followed by desulfonylation with 5percent hydrochloric acid in tetrahydrofuran, afforded 3-(cis-3-hexenyl)-2-cyclopentenone in a good yield.The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5percent sodium hydroxide yielded cis-jasmone in a 80percent yield.
A NEW PROCEDURE FOR DESULFONYLATION: PREPARATION OF β-SUBSTITUTED α,β-UNSATURATED KETONES AND ALDEHYDES
Yoshida, Takashi,Saito, Shojiro
, p. 165 - 168 (2007/10/02)
The treatment of the tert-alkyl sulfones bearing carbonyl group at the β-position with 5 percent hydrochloric acid in THF at 30 - 65 deg C afforded β-substituted α,β-unsaturated ketones and aldehydes in excellent yields.
