104316-95-2

Upstream product

• 104316-84-9 4-chlorophenylthiomethyl trifluoroacetate 
• 934-73-6 methyl 4-chlorophenyl sulfoxide 
• 111-81-9 Methyl 10-undecenoate 
• 112474-77-8 methyl 12-(4-chlorophenylthio)dodec-3-enoate 

Downstream Products

• 40264-97-9 methyl 9,11-undecadienoate 
• 40264-97-9 (Z)-Undeca-8,10-dienoic acid methyl ester 

Relevant academic research and scientific papers

"Ene"-Type Reaction of the Pummerer Rearrangement Product Derived from 4-Chlorophenyl Methyl Sulphoxide: Synthesis of Some Insect Sex Pheromones

The Pummerer rearrengement product (8) derived from 4-chlorophenyl methyl sulphoxide (7) and trifluoroacetic anhydride undergoes an ene type reaction with terminal olefins to give the products (9).Oxidation of (9) followed by thermolysis of the resultant sulphoxides provides a general synthesis of the terminal conjugated dienes (10).Using this method, dodeca-9,11-dienyl acetate (16), the sex pheromone of the red bollworm moth, has been prepared.Transformations of the ene products (9) to some other insect sex pheromones such as bombykol (20) and tetradec-11-enyl acetate (24) are also described.

NOVEL SYNTHESIS OF 1,3-DIENES FROM 1-ALKENES VIA "ENE" REACTION WITH PUMMERER REARRANGEMENT PRODUCT: A SHORT SYNTHESIS OF THE SEX PHEROMONE OF THE RED BOLLWORM MOTH

A Pummerer rearrangement product, 4-chlorophenylthiomethyl trifluoroacetate (6), obtained from 4-chlorophenyl methyl sulfoxide (5) and trifluoroacetic anhydride, reacted with 1-alkenes in trifluoroacetic acid to give the ene products 8, which were readily converted into terminal 1,3-dienes 10 by oxidation and subsequent pyrolysis.Using this method, 9,11-dodecadien-1-yl acetate (12), a sex pheromone of the red bollworm moth, was synthesized.