Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1989-12-14
1991-01-08
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
549214, 549221, 549408, 549410, 549414, 549462, 549470, 549510, 549511, 556446, 558 37, 558194, 560108, 560140, C07C 4118
Patent
active
049837796
ABSTRACT:
An improved process for the preparation of vinyl ethers by the coupling reaction of an ester of the formula ##STR1## with a carbonyl containing compound of the formula ##STR2## wherein A and R are passive organic groups and OY is a hydroxyl group or OP where P is a protecting group is described. The ester and the carbonyl containing compound are reacted in an organic solvent with a titanium salt, a metallic reducing agent and an amine base to provide the vinyl ether. The reaction is safe and produces high yields. The vinyl ethers are useful for producing dioxetanes which produce light upon triggering.
REFERENCES:
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McMurry et al., Acc. Chem. Res. 16, 405-411 (1983).
Dams et al., J. Org. Chem. 47, 248-259 (1982).
McMurry et al., J. Org. Chem. 43, 3255-3266 (1978).
Mukaiyama et al., Chem. Lett. 1041-1044 (1973).
McMurry et al., JACS 96, 4708-4709 (1974).
Tyrlik et al., Bull. Soc. Chim. Fr. 6, No. 2147-2148 (1973).
McLeod Ian C.
Raymond Richard L.
The Board of Governors of Wayne State University
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