Julia, Marc published the artcileSyntheses via sulfones. XXXVII. Synthesis of three pheromones with a Z double bond: (Z)-8-DDA, (Z)-9-DDA, and (Z)-9-TDA, Application of (Z)-Dodec-9-en-1-yl acetate, the publication is Tetrahedron (1986), 42(9), 2469-74, database is CAplus.
The title compounds, Z-8-dodecen-1-yl acetate, Z-9-dodecen-1-yl acetate, and Z-9-tetradecen-1-yl acetate, have been synthesized in 3 efficient steps. The reaction mixture from lithiated HO(CH2)nSO2Ph (n = 8, 9) and Me(CH2)mCHO (m = 1-3) was quenched with Ac2O yielding a diastereoisomeric mixture of β-acetoxy sulfones. Convergent elimination with powd. NaOH led to E-Me(CH2)mCH:C(SO2Ph)(CH2)n-1OAc. Stereospecific hydrogenolysis of the sulfonyl group was carried out with sodium dithionite leading to the unsaturated alcs. (>99% Z), which were reesterified.
Tetrahedron published new progress about 16974-11-1. 16974-11-1 belongs to esters-buliding-blocks, auxiliary class Aliphatic Chain, name is (Z)-Dodec-9-en-1-yl acetate, and the molecular formula is C14H26O2, Application of (Z)-Dodec-9-en-1-yl acetate.
Referemce:
https://en.wikipedia.org/wiki/Ester,
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