80945-24-0

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 943-92-0 ethyl 2-(trimethylsilylmethyl)cyclopropanecarboxylate 
• 55454-02-9 sodium salt of methyl phenyl sulfone 

Downstream Products

• 89664-40-4 (1-Benzenesulfonyl-2-methyl-cyclopropyl)-(2-trimethylsilanylmethyl-cyclopropyl)-methanone 
• 80945-32-0 6-phenylsulfonyl-1-undecen-5-one 
• 113115-59-6 1-Benzenesulfonyl-hexane-2,5-dione 
• 80945-33-1 1-Methyl-1-(phenylsulfonyl)-5-hexen-2-one 
• 74420-28-3 6-(Phenylsulfonyl)undecane-2,5-dione 
• 80945-29-5 2-(trimethylsilylmethyl)-1-(1-oxo-2-phenylsulfonylpropyl)cyclopropane 
• 80945-31-9 6-(phenylsulfonyl)-1-hexen-5-one 
• 80945-25-1 2-(trimethylsilylmethyl)-1-(1-oxo-2-phenylsulfonylheptyl)cyclopropane 

Relevant academic research and scientific papers

Silicon-Assisted Ring Opening of Cyclopropyl Ketones with Boron Trifluoride-Acetic Acid Complex

2-(Trimethylsilylmethyl)cyclopropyl ketones were smoothly cleaved with boron trifluoride-acetic acid complex under mild reaction conditions with the assistance of the trimethylsilyl group to give γ,δ-enones in good yields.The major effect of the trimethylsilyl group in the ring opening of the cyclopropyl ketones was unambiguously confirmed in the dicyclopropyl ketone 15: one of its two cyclopropyl rings, which has a trimethylsilylmethyl group, was selectively cleaved.Furthermore, the reaction was applied to the formal total synthesis of cis-jasmone.Keywords - ring opening of cyclopropyl ketone; trimethylsilyl group; γ,δ-enone; cis-jasmone; allylsilane; boron trifluoride-acetic acid

RING OPENING OF CYCLOPROPYL KETONES ASSISTED BY THE TRIMETHYLSILYL GROUP

Cyclopropyl ketones 2 were smoothly cleaved with boron trifluoride-acetic acid under mild reaction conditions by the assistance of trimethylsilyl group to give γ,δ-enones in good yields and the reaction was applied to the formal total synthesis of cis-jasmone.