Formation of electron deficient α,β oxygenated alkenes

CHED 579

Michael J. Caspers, mikecaspers@hotmail.com and Craig P. Jasperse, jasperse@mnstate.edu. Department of Chemistry, Minnesota State University Moorhead, 1104 7th Ave. S, Moorhead, MN 56563
A family of alkoxyalkenes 4 has been formed through a quick procedure. The novel alkyne 3 can be conveniently made in good yield. The solvent used in the chlorination of propiolic acid 1 is critical. There has been no problems with sterics or any problem preventing the type of alcohol being added to the alkyne 3 to make the final products 4. E/Z ratios are high, and E/Z isomers of 4 are easily separable. For the ester analogs the E/Z ratios are mediocre and isomers are not easily separable. Products 4 and related substrates are being investigated for their reactivity towards Grignard reagents, Diels-Alder reactions, and Pauson-Kahn cyclization reactions.