31089-90-4Relevant articles and documents
SYNTHESIS OF α-DAMASCONE AND 1-(2,6,6-TRIMETHYL-2-TETRAHYDROPYRANYL)-2-ALKEN-1-ONES
Erman, M. B.,Pribytkova, I. M.,Gulyi, S. E.,Bogomolova, O. A.,Cherkaev, G. V.,et al.
, p. 2294 - 2301 (2007/10/02)
α-Damascone was obtained by the reaction of α-cyclocitral with allyl bromide in the presence of zinc, followed by oxidation of the obtained alcohol with chromic acid to the ketone and isomerization of the latter with triethylamine as catalyst.The analogous synthesis of β-damascone from 1-(4,6,6-trimethyl-1,3-cyclohexadienyl)-2-buten-1-one was impossible on account of complications at the oxidation stage.The rearrangement of the acetylenic alcohols with polyvanadioorganosiloxane as catalyst led to 1-(2,6,6-trimethyl-2-tetrahydropyranyl)-2-alken-1-ones.
172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone
Snowden, Roger L.,Linder, Simon M.,Muller, Bernard L.,Schulte, Karl H.
, p. 1858 - 1878 (2007/10/02)
The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).
Process for the preparation of polyunsaturated cycloaliphatic ketones
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, (2008/06/13)
Polyunsaturated ketones of formula STR1 having a double bond in position 2' or 3' of the side chain and possessing either an isolated double bond in position 1 or 2, or two conjugated double bonds in positions 1 and 3 of the ring, as indicated by the dotted lines, and wherein index n stands for integer 1 or 2, and each of the symbols R1 to R7, identical or different, designates a hydrogen atom or a lower alkyl radical, are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.