Photochemical synthesis of 3-Alkynals from 1-Alkynoxy-9, 10-anthraquinones

…, PJ Boldenow, EC Hansen, JM Kallemeyn…

Index: Blankespoor, Ronald L.; DeVries, Tim; Hansen, Eric; Kallemeyn, Jeffrey M.; Klooster, Aaron M.; Mulder, Jason A.; Smart, Robert P.; Vander Griend, Douglas A. Journal of Organic Chemistry, 2002 , vol. 67, # 8 p. 2677 - 2681

Full Text: HTML

Citation Number: 4

Abstract

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.