The photochemical reactions of substituted acetones with triethyl phosphite
1968; Elsevier BV; Volume: 24; Issue: 17 Linguagem: Inglês
10.1016/s0040-4020(01)96304-5
ISSN1464-5416
AutoresH. TOMIOKA, Yasuji Izawa, Y. OGATA,
Tópico(s)Chemical Reactions and Mechanisms
ResumoPhotochemical reactions of substituted acetones with triethyl phosphite have been studied to investigate the chemical behaviour of the n-π* excited state of the CO group. UV irradiation of an ethereal solution of chloroacetone (Ia) and triethyl phosphite (II) at 20° gives vinyl phosphate (III) and ketophosphonate (IV), together with other by-products. The yield of IV decreases by addition of a radical scavenger, hydroquinone, whereas the yield of III is little affected. Addition of methanol and acetic acid suppresses the reaction. A similar reaction is possible with other substituted acetones. The ratio of [III]/[IV] varies with derivatives of acetones. A probable mechanism is discussed.
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