Solvolytic cleavage of alkenylpentafluorosilicates catalyzed by copper(II) acetate. A stereoselective synthesis of (E)-alkenyl ethers from alkynes
作者:Kohei Tamao、Toshio Kakui、Makoto Kumada
DOI:10.1016/0040-4039(80)88078-6
日期:1980.1
(E)-Alkenylpentafluorosilicates, obtainable from acetylenes via hydrosilylation-silicate formation, react with alcohols in the presence of a catalytic amount of copper(II) acetate under an atmosphere of air (oxygen) at room temperature to form (E)-alkenyl ethers stereoselectively in satisfactory yields. Similar reaction with water gives aldehydes.
Acyclic enol ethers, isomers thereof, organoleptic uses thereof and processes for preparing same
申请人:——
公开号:US20040013779A1
公开(公告)日:2004-01-22
Described are synthetically produced substantially pure enol ether compositions which are cis and/or trans isomers of enol ethers having the structures:
1
wherein R
1
is C
4
-C
10
straight chain alkyl or C
9
8-alkenyl; and wherein R
2
is C
1
-C
4
alkyl, C
3
-C
4
2-alkenyl, C
4
3-alkenyl or C
10
non-allenic alkadienyl and uses thereof in imparting, augmenting or enhancing the aroma and/or taste of a consumable material such as a perfume composition, a cologne, a perfumed article such as a soap, cosmetic, hair preparation or detergent, a foodstuff, a chewing gum or an alcoholic or non-alcoholic beverage such as a carbonated beverage or fruit liquer. Also described is a process for synthesis of such enol ethers by means of (i) first forming an acetal having the structure:
R
1
—CH
2
—CH(OR
2
)
2
(ii) then carrying out a thermal decomposition reaction at pH<7 and then (iii) fractionally distilling the resulting reaction product to provide the enol ether.