Stereoselective synthesis of (E)-, (E,Z)- and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step was written by Yamada, Sachiko;Ohsawa, Hideto;Suzuki, Takayoshi;Takayama, Hiroaki. And the article was included in Journal of Organic Chemistry in 1986.Computed Properties of C14H24O2 The following contents are mentioned in the article:
A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step. Direct alkylation of 3-sulfolene I (R = H) (II) at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78°. Alkylation of 2-alkyl-3-sulfolenes I (R = alkyl) give trans-2,5-dialkyl-3-sulfolenes III (R, R1 = alkyl) with 100% regioselectivity and more than 90% stereoselectivity. Desulfonylation of III was examined and the conditions to give stereoselectively the corresponding (E,Z)- and (E,E)-conjugated dienes were found. Three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, were synthesized by starting from II with nearly 100% stereoselectivity. Cyclohexenes IV (R = alkyl) were prepared from the corresponding I via a Diels-Alder reaction with maleic anhydride. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Computed Properties of C14H24O2).
(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Computed Properties of C14H24O2
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics