219601-21-5

Upstream product

• 442159-98-0 1-(phenylsulfinyl)-2-hexanol 
• 442159-99-1 2-mesyloxy-1-(phenylsulfinyl)hexane 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 110-62-3 pentanal 
• 50746-65-1 Diethyl (phenylsulfinyl)methylphosphonate 

Downstream Products

• 219601-28-2 (2-Benzenesulfinylmethyl-1,1-difluoro-hexyl)-phosphonic acid diethyl ester 
• 442160-03-4 (1E)-1-phenyl-4-(phenylsulfinyl)-1,4-nonadien-3-ol 
• 442160-26-1 1-phenyl-4-(phenylsulfinyl)-4-nonen-3-ol 
• 442160-39-6 1-phenyl-4-(phenylsulfinyl)-4-nonen-1-yn-3-ol 
• 442160-27-2 3-mesyloxy-1-phenyl-4-(phenylsulfinyl)-4-nonene 
• 442160-40-9 3-acetoxy-1-phenyl-4-(phenylsulfinyl)-4-nonen-1-yne 
• 442160-04-5 (1E)-3-acetoxy-1-phenyl-4-(phenylsulfinyl)-1,4-nonadiene 
• 67647-96-5 nona-3,4-dien-1-ylbenzene 

Relevant academic research and scientific papers

A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant

The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.

A conjugate addition/sulfoxide elimination route to allylic difluorophosphonates

Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluoromethyllithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sulfoxide elimination afforded the products of formal vinylation, attaching the difluoromethylenephosphonato group to an alkenyl carbon atom. With acyclic vinyl sulfoxides, the addition occurred in moderate to poor yield. Addition failed completely in the absence of cerium(III) chloride, and was facilitated by an excess of the reagent.