Photochemical synthesis of 3-alkynals from 1-alkynoxy-9,10-anthraquinones.
Photolysis of 1-(3-alkynoxy)-9,10-anthraquinones in deoxygenated methanol leads to moderate yields (35-45%) of 3-alkynals along with the unexpected formation of diacetals. Reaction of these 3-alkynals with Grignard and Wittig reagents occurs nearly quantitatively without rearrangement to their 2,3-dienal isomers.
Blankespoor
Ronald L
RL
Department of Chemistry and Biochemistry, Calvin College, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546-4403, USA. blan@calvin.edu
Boldenow
Peter J
PJ
Hansen
Eric C
EC
Kallemeyn
Jeffrey M
JM
Lohse
Andrew G
AG
Rubush
David M
DM
Vrieze
Derek
D