Tellurolate-induced 1,4-elimination of 1,4-dibromo 2-enes. Syntheses of 1,3-dienes was written by Engman, Lars;Bystroem, Styrbjoern E.. And the article was included in Journal of Organic Chemistry in 1985.Electric Literature of C14H24O2 The following contents are mentioned in the article:
Na 2-thiophenetellurolate (I), generated in catalytic amounts from bis(2-thienyl) ditelluride by NaBH4, debrominated 1,4-dibromo-2-olefins, e.g., BrCH2CH:CHCHRBr [II, R = Et, Bu, Me(CH2)n, AcO(CH2)m; n = 6, 8; m = 7, 8] to 1,3-dienes under mild conditions. The required II were prepared by allylic α,α’-bromination of olefins by N-bromosuccinimide. Terminal olefins yielded, via allylic rearrangement, a mixture of II and 1,2-dibromo-3-olefins. Both isomers were converted to 1,3-dienes (E/Z â?9/1) by I. The synthetic utility of the tellurolate-induced debromination was demonstrated in a 2-step synthesis of (E)-CH2:CHCH:CH(CH2)8OAc, the main component of the red bollworm moth sex pheromone. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Electric Literature of C14H24O2).
(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Electric Literature of C14H24O2
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics