SUBSTITUENT EFFECTS ON PHOSPHONATION OF γ-CHLOROPROPYL ARYL KETONES WITH TRIETHYL PHOSPHITE

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 131; no. 1; pp. 129 - 139
• Main Authors: Yu, Jen-Wen, Shih, Chung-Chieh, Huang, Steve K.
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01.12.1997
• Subjects: Carbonyl group-assisted mechanism; Oxycyclopentyl phosphonate; Substituent effect: Rate constant; γ-Ketophosphonate

Phosphonation of γ-chloropropyl aryl ketones 1 with triethyl phosphite yielded oxycyclopentyl phosphonates 2 and γ-ketophosphonates 3. Formation of 2 was greatly facilitated by the presence of electron-releasing p-substituents on the phenyl group, particularly the methoxy group, which may delocalize...