Vapor phase photochemistry of dimethylpyrazines and dimethylpyrimidines

ORGN 507

James W. Pavlik, jwpavlik@wpi.edu and Tharinee Vongnakorn, tharinee@wpi.edu. Department of Chemistry and Biochemistry, Worcester Polytechnic Institute, 100 Institute Road, Worcester, MA 01609
The photochemistry of the three dimethylpyrazines(1-3) and the four dimethylpyrimidines(4-7) has been studied by irradiating each isomer at 254 nm in the vapor phase. The primary interconversions are summarized below. Thus, 3,6 and 7 constitute a triad while 1,2,4 and 5 constitute a tetrad. Irradiation of any one member of either group leads to the formation of the other members of the group. The isomerizations include pyrazine to pyrimidine; pyrimidine to pyrazine; and pyrimidine to pyrimidine. 4 also transposes to 8 in a unique pyrimidine to pyridazine isomerization. Irradiation of 8 results in formation of 1, 2, 4 and 5, the members of the tetrad.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007