181576-35-2

Upstream product

• 152455-13-5 1-methyl-2,5-cyclohexadiene-1-carboxaldehyde 
• 1014-93-3 1-(benzyloxy)-5-bromopentane 
• 181576-34-1 (Z)-6-(1-Methylcyclohexa-2,5-dienyl)hex-5-en-1-ol 
• 252869-48-0 3-Methyl-3-[(Z)-6-(phenylsulfenyl)hex-1-enyl]cyclohexa-1,4-diene 

Downstream Products

• 181576-36-3 4-Methyl-4-[(Z)-6-(phenylsulfonyl)hex-1-enyl]cyclohexa-2,5-dienone 

Relevant academic research and scientific papers

Hexamethyldisilazanes mediated one-pot intramolecular Michael addition-olefination reactions leading to exo-olefinated bicyclo[6.4.0]dodecanes

A novel one-pot reaction for the synthesis of exo-olefinated bicyclo[6.4.0]dodecanes 23 has been developed on the basis of an intramolecular Michael reaction of phenylsulfonyl compounds 4 with potassium hexamethyldisilazide (KHMDS) and a sequential reaction with an excess of methoxymethyl chloride (MOMCl). By this reaction, an exo-olefin group was regioselectively introduced at the α-position to the carbonyl group in the 6-membered ring in high yield. The regioselective introduction of the olefin moiety could be envisaged to proceed through a Mannich-type reaction involving the aminomethylating agent 24, which, in turn, is generated in situ by the action of HMDS on MOMCl. The Royal Society of Chemistry 1999.

Facile construction of the bicyclo[6.4.0]dodecane system by the intramolecular Michael addition of sulfonyl carbanion

A bicyclo [6.4.0] dodecane system is synthesised via the intramolecular Michael addition of sulfonyl carbanion.