Oxidation of aromatic compounds: XIV. Oxidation of arylethynyl ketones in the system CF3CO2H-CH2Cl2-PbO 2

Article abstract of DOI:10.1134/S1070428006010118

Oxidation of arylethynyl ketones ArC=CCOCX₃ (X = H, F) in the system CF₃CO₂H-CH₂Cl₂-PbO ₂ was studied on a preparative scale. The oxidation of 4-arylbut-3-yn-2-ones (X = H) involves transfe

Full text of DOI:10.1134/S1070428006010118

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ꢄꢁ-ꢁ ꢁꢐꢊꢃꢁ+]ꢉꢊꢁ &ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁꢍꢅꢊꢀꢂꢄꢁ
ꢇꢇꢊꢋꢆꢄꢁ ꢐꢐꢊꢅꢍꢄꢁ ꢃꢂꢊꢇꢆꢄꢁ ꢂꢂꢂꢊꢀꢅꢄꢁ ꢂꢂꢋꢊꢍꢀꢄꢁ ꢂꢍꢇꢊꢂꢂꢄꢁ ꢂꢀꢂꢊꢀꢏꢄꢁ
+
ꢂꢐꢋꢊꢀꢍꢊꢁ
ꢈꢉꢊꢃꢅꢈꢉ'LPHWKR[\SKHQ\OꢋEXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,Eꢋꢁꢁ
<LHOGꢁꢍꢏ<ꢄꢁPSꢁꢂꢆꢆ±ꢂꢆꢅƒ&ꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁ
SSPꢓꢁꢅꢊꢋꢍꢁVꢁꢈꢍ+ꢄꢁ0HꢉꢄꢁꢍꢊꢐꢐꢁVꢁꢈꢍ+ꢄꢁ20HꢉꢄꢁꢍꢊꢃꢂꢁVꢁꢈꢍ+ꢄꢁ
20HꢉꢄꢁꢀꢊꢐꢇꢁGꢁꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢐꢊꢂꢁ+]ꢉꢄꢁꢏꢊꢆꢇꢁVꢁꢈꢂ+ꢄꢁ
+
ꢉꢄꢁꢏꢊꢅꢂꢁGꢁꢈꢂ+ꢄꢁ+
ꢄꢁ-ꢁ ꢁꢐꢊꢂꢁ+]ꢉꢊꢁ)RXQGꢄꢁ<ꢓꢁꢁ
&ꢁꢏꢂꢊꢆꢅꢒꢁ+ꢁꢀꢊꢂꢅꢊꢁ& + 2 ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ&ꢁꢏꢆꢊꢇꢏꢒꢁꢁ
+ꢁꢇꢊꢃꢅꢊꢁꢁ
ꢈꢉꢊꢄꢅꢈꢉ'LPHWK\OSKHQ\OꢋꢉꢇꢅꢇꢅꢇꢉWULIOXRUREXWꢉꢃꢉ\Qꢉ
ꢄꢉRQH ꢊ,,Fꢋꢁꢁ <LHOGꢁ ꢋꢅ<ꢄꢁ RLO\ꢁ VXEVWDQFHꢄꢁ ESꢁ ꢀꢆ±ꢀꢅƒ&ꢁ
ꢈꢆꢊꢇꢁPPꢉꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁꢂꢀꢃꢆꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁ
ꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁꢅꢊꢍꢋꢁVꢁꢈꢍ+ꢄꢁ0Hꢉꢄꢁ
ꢅꢊꢋꢅꢁVꢁꢈꢍ+ꢄꢁ0HꢉꢄꢁꢀꢊꢃꢋꢁGꢁꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢏꢊꢀꢁ+]ꢉꢄꢁꢏꢊꢆꢅꢁVꢁ
ꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢏꢊꢍꢋꢁGꢁꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢏꢊꢀꢁ+]ꢉꢊꢁ)RXQGꢄꢁ<ꢓꢁ
& ꢁ ꢀꢍꢊꢐꢀꢒꢁ +ꢁ ꢋꢊꢂꢇꢊꢁ & + ) 2ꢊꢁ &DOFXODWHGꢄꢁ <ꢓꢁ &ꢁꢀꢍꢊꢏꢅꢒꢁꢁ
+ꢁꢋꢊꢆꢂꢊꢁꢁ
ꢈꢉꢊꢃꢅꢈꢉ0HWK\OHQHGLR[\SKHQ\OꢋEXWꢉꢃꢉ\QꢉꢄꢉRQH
ꢊ,Fꢋꢁꢁ<LHOGꢁꢍꢋ<ꢄꢁPSꢁꢏꢀ±ꢏꢐƒ&ꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁ
SSPꢓꢁꢅꢊꢋꢂꢁVꢁꢈꢍ+ꢄꢁ0HꢉꢄꢁꢀꢊꢆꢂꢁVꢁꢈꢅ+ꢄꢁ2&+ 2ꢉꢄꢁꢀꢊꢏꢃꢁGꢁ
ꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢐꢊꢂꢁ+]ꢉꢄꢁꢀꢊꢃꢐꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢏꢊꢂꢍꢁGꢁꢁ
ꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢐꢊꢂꢁ+]ꢉꢊꢁ)RXQGꢄꢁ<ꢓꢁ&ꢁꢏꢆꢊꢋꢍꢒꢁ+ꢁꢋꢊꢂꢀꢊꢁ
& + 2 ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ&ꢁꢏꢆꢊꢅꢂꢒꢁ+ꢁꢋꢊꢅꢃꢊꢁꢁ
ꢈꢉꢊꢄꢅꢈꢉ'LPHWK\OSKHQ\OꢋEXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,Gꢋꢁꢁ<LHOGꢁ
ꢋꢐ<ꢄꢁRLO\ꢁVXEVWDQFHꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁꢂꢀꢀꢆꢁ
ꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁꢅꢊꢍꢋꢁVꢁ
ꢈꢍ+ꢄꢁ0HꢉꢄꢁꢅꢊꢋꢋꢁVꢁꢈꢀ+ꢄꢁ0HꢉꢄꢁꢀꢊꢃꢃꢁGꢁꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢁ
ꢐꢊꢆꢁ+]ꢉꢄꢁꢏꢊꢆꢀꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢏꢊꢋꢂꢁGꢁꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢁ
ꢐꢊꢆꢁ+]ꢉꢊꢁ)RXQGꢄꢁ<ꢓꢁ&ꢁꢐꢋꢊꢆꢆꢒꢁ+ꢁꢀꢊꢐꢃꢊꢁ& + 2ꢊꢁ&DOꢌ
FXODWHGꢄꢁ<ꢓꢁ&ꢁꢐꢍꢊꢀꢃꢒꢁ+ꢁꢏꢊꢆꢅꢊꢁꢁ
ꢈꢉꢊꢈꢉ0HWK\OSKHQ\OꢋEXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,Hꢋꢁꢁ<LHOGꢁ
ꢀꢅ<ꢄꢁRLO\ꢁVXEVWDQFHꢄꢁESꢁꢃꢇƒ&ꢁꢈꢅꢁPPꢉꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁ
FP ꢓꢁ ꢂꢀꢏꢇꢁ ꢈ& 2ꢉꢄꢁ ꢅꢅꢆꢆꢁ ꢈ& &ꢉꢊꢁ +ꢁ 105ꢁ VSHFWUXPꢄꢁꢁ
ꢄꢁSSPꢓꢁꢅꢊꢍꢇꢁVꢁꢈꢍ+ꢄꢁ0HꢉꢄꢁꢅꢊꢋꢂꢁVꢁꢈꢍ+ꢄꢁ0HꢉꢄꢁꢏꢊꢂꢀꢁGꢁꢁ
ꢈꢅ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢏꢊꢃꢁ+]ꢉꢄꢁꢏꢊꢋꢋꢁGꢁꢈꢅ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢏꢊꢃꢁ+]ꢉꢁ
ꢈFIꢊꢁ>ꢂꢃ@ꢉꢊꢁ
ꢈꢉ3KHQ\OEXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,Iꢋꢁꢁ<LHOGꢁꢏꢆ<ꢄꢁESꢁꢏꢆƒ&ꢁ
ꢈꢅꢁ PPꢉꢒꢁ SXEOLVKHGꢁ GDWDꢁ>ꢅꢆ@ꢓꢁ ESꢁ ꢂꢋꢂƒ&ꢁ ꢈꢅꢇꢁ PPꢉꢊꢁ ,5ꢁ
VSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁꢂꢀꢀꢇꢁꢈ& 2ꢉꢄꢁꢅꢅꢆꢆꢁꢈ& &ꢉꢊꢁ
ꢇꢅꢇꢅꢇꢉ7ULIOXRURꢉꢈꢉꢊꢈꢉPHWKR[\SKHQ\OꢋEXWꢉꢃꢉ\Qꢉꢄꢉ
RQH ꢊ,,Dꢋꢁꢁ<LHOGꢁꢋꢅ<ꢄꢁRLO\ꢁVXEVWDQFHꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁ
FP ꢓꢁꢂꢀꢃꢆꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁ
SSPꢓꢁꢍꢊꢐꢇꢁVꢁꢈꢍ+ꢄꢁ20HꢉꢄꢁꢀꢊꢃꢅꢁGꢁꢈꢅ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢐꢊꢂꢁ+]ꢉꢄꢁ
ꢏꢊꢀꢆꢁ Gꢁ ꢈꢅ+ꢄꢁ + ꢄꢁ -ꢁ ꢁ ꢐꢊꢂꢁ +]ꢉꢊꢁ )ꢁ 105ꢁ VSHFWUXPꢓꢁꢁ
ꢁ±ꢏꢋꢊꢋꢁSSPꢄꢁVꢁꢈꢍ)ꢄꢁ&2&) ꢉꢊꢁ &ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁ
SSPꢓꢁꢇꢇꢊꢋꢇꢁTꢁꢈ-ꢁ ꢁꢂꢋꢇꢊꢆꢁ+]ꢉꢄꢁꢐꢋꢊꢆꢀꢁVꢄꢁꢂꢆꢅꢊꢋꢐꢁWꢁꢈ-ꢁ ꢁꢁ
ꢋꢊꢏꢁ+]ꢉꢄꢁꢂꢆꢃꢊꢀꢅꢁWꢁꢈ-ꢁ ꢁꢐꢊꢇꢁ+]ꢉꢄꢁꢂꢂꢋꢊꢏꢋꢁGꢊGꢁꢈ-ꢁ ꢁꢂꢀꢅꢊꢀꢄꢁ
ꢋꢊꢇꢁ +]ꢉꢄꢁ ꢂꢂꢋꢊꢃꢏꢁ Tꢁ ꢈ-ꢁ ꢁ ꢅꢐꢐꢊꢋꢁ +]ꢉꢄꢁ ꢂꢍꢀꢊꢅꢐꢁ GꢊGꢁ ꢈ-ꢁ ꢁ
ꢂꢀꢋꢊꢇꢄꢁ ꢏꢊꢆꢁ +]ꢉꢄꢁ ꢂꢀꢍꢊꢅꢍꢁ Pꢄꢁ ꢂꢀꢀꢊꢃꢇꢁ Tꢁ ꢈ-ꢁ ꢁ ꢋꢂꢊꢐꢁ +]ꢉꢊꢁ
0DVVꢁVSHFWUXPꢓꢁPꢑ]ꢁꢅꢅꢐꢁ>0@ ꢊꢁ)RXQGꢄꢁ<ꢓꢁ&ꢁꢇꢐꢊꢆꢋꢒꢁꢁ
+ꢁꢅꢊꢃꢏꢊꢁ& + ) 2ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ&ꢁꢇꢏꢊꢃꢆꢒꢁ+ꢁꢍꢊꢆꢃꢊꢁꢁ
ꢈꢉꢊꢃꢅꢈꢉ'LPHWKR[\SKHQ\OꢋꢉꢇꢅꢇꢅꢇꢉWULIOXRUREXWꢉꢃꢉ
\QꢉꢄꢉRQH ꢊ,,Gꢋꢁꢁ<LHOGꢁꢇꢇ<ꢄꢁPSꢁꢀꢂ±ꢀꢅƒ&ꢊꢁ,5ꢁVSHFWUXPꢄꢁ
ꢄꢁFP ꢓꢁꢂꢀꢃꢇꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ
ꢄꢁSSPꢓꢁꢍꢊꢃꢆꢁVꢁꢈꢍ+ꢄꢁ20HꢉꢄꢁꢍꢊꢃꢋꢁVꢁꢈꢍ+ꢄꢁ20HꢉꢄꢁꢀꢊꢐꢃꢁGꢁ
ꢈꢂ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢐꢊꢋꢁ+]ꢉꢄꢁꢏꢊꢆꢃꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢏꢊꢍꢇꢁGꢁꢈꢂ+ꢄꢁ
+
ꢄꢁ-ꢁ ꢁꢐꢊꢋꢁ+]ꢉꢊꢁ0DVVꢁVSHFWUXPꢓꢁPꢑ]ꢁꢅꢇꢐꢁ>0@ ꢊꢁ
)RXQGꢄꢁ<ꢓꢁ&ꢁꢇꢇꢊꢋꢆꢒꢁ+ꢁꢍꢊꢀꢅꢊꢁ& + ) 2 ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ
&ꢁꢇꢇꢊꢐꢅꢒꢁ+ꢁꢍꢊꢇꢂꢊꢁꢁ
ꢇꢅꢇꢅꢇꢉ7ULIOXRURꢉꢈꢉꢊꢄꢉPHWK\OꢉꢈꢅꢌꢉPHWK\OHQHGLR[\ꢉ
SKHQ\OꢋEXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,,Hꢋꢁꢁ<LHOGꢁꢅꢀ<ꢄꢁPSꢁꢀꢅ±ꢁ
ꢀꢋƒ&ꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁꢂꢀꢃꢇꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ
+ꢁ 105ꢁ VSHFWUXPꢄꢁ ꢄꢁ SSPꢓꢁ ꢅꢊꢋꢋꢁ Vꢁ ꢈꢍ+ꢄꢁ 0Hꢉꢄꢁ ꢀꢊꢆꢅꢁ Vꢁ
ꢈꢅ+ꢄꢁ2&+ 2ꢉꢄꢁꢀꢊꢏꢋꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢀꢊꢃꢐꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢊꢁ
&ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁꢅꢆꢊꢋꢅꢄꢁꢐꢏꢊꢇꢃꢄꢁꢂꢆꢂꢊꢇꢀꢄꢁ
ꢂꢆꢅꢊꢆꢐꢄꢁꢂꢂꢆꢊꢆꢆꢄꢁꢂꢂꢆꢊꢋꢃꢄꢁꢂꢂꢅꢊꢐꢐꢄꢁꢂꢂꢇꢊꢆꢋꢁTꢁꢈ-ꢁ ꢁꢅꢐꢐꢊꢃꢁ+]ꢉꢄꢁ
ꢂꢋꢂꢊꢇꢄꢁꢂꢋꢇꢊꢃꢀꢄꢁꢂꢇꢂꢊꢃꢃꢄꢁꢂꢀꢀꢊꢐꢆꢁTꢁꢈ-ꢁ ꢁꢍꢆꢊꢃꢁ+]ꢉꢊꢁ0DVVꢁ
VSHFWUXPꢓꢁPꢑ]ꢁꢅꢇꢀꢁ>0@ ꢀꢁ)RXQGꢄꢁ<ꢓꢁ&ꢁꢇꢇꢊꢃꢐꢒꢁ+ꢁꢍꢊꢆꢅꢊꢁ
& + ) 2 ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ&ꢁꢇꢀꢊꢅꢀꢒꢁ+ꢁꢅꢊꢏꢇꢊꢁꢁ
ꢈꢉꢊꢃꢅꢈꢉ'LPHWKR[\ꢉꢍꢉQLWURSKHQ\OꢋꢉꢇꢅꢇꢅꢇꢉWULIOXRURꢉ
EXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,,Iꢋꢁꢁ<LHOGꢁꢀꢋ<ꢄꢁPSꢁꢂꢅꢂ±ꢂꢅꢍƒ&ꢊꢁꢁ
+ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁꢋꢊꢆꢂꢁVꢁꢈꢍ+ꢄꢁ20HꢉꢄꢁꢋꢊꢆꢅꢁVꢁ
ꢈꢍ+ꢄꢁ20HꢉꢄꢁꢏꢊꢂꢋꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢄꢁꢏꢊꢏꢏꢁVꢁꢈꢂ+ꢄꢁ+ ꢉꢊꢁ )ꢁ
105ꢁ VSHFWUXPꢓꢁ ꢁ ±ꢏꢋꢊꢅꢁ SSPꢄꢁ Vꢁ ꢈꢍ)ꢄꢁ & 2& )ꢉꢊꢁ 0DVVꢁ
VSHFWUXPꢄꢁPꢑ]ꢓꢁꢍꢆꢍꢁ>0@ ꢀꢁ)RXQGꢄꢁ<ꢓꢁ&ꢁꢋꢏꢊꢏꢏꢒꢁ+ꢁꢅꢊꢐꢃꢒꢁ
1ꢁꢋꢊꢏꢆꢊꢁ& + ) 12 ꢊꢁ&DOFXODWHGꢄꢁ<ꢓꢁ&ꢁꢋꢏꢊꢇꢋꢒꢁ+ꢁꢅꢊꢀꢀꢒꢁ
1ꢁꢋꢊꢀꢅꢊꢁꢁ
ꢇꢅꢇꢅꢇꢉ7ULIOXRURꢉꢈꢉ>ꢄꢅꢃꢅꢌꢅꢍꢉWHWUDPHWK\Oꢉꢈꢉꢊꢈꢅꢈꢅꢈꢉ
WULIOXRURꢉꢃꢉR[REXWꢉꢇꢉ\Q\OꢋSKHQ\O@EXWꢉꢃꢉ\QꢉꢄꢉRQH
ꢊ,,Jꢋꢁ <LHOGꢁꢅꢂ<ꢄꢁPSꢁꢂꢂꢐ±ꢂꢅꢆƒ&ꢊꢁ,5ꢁVSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁ
ꢇꢅꢇꢅꢇꢉ7ULIOXRURꢉꢈꢉꢊꢃꢉIOXRURꢉꢈꢉPHWKR[\SKHQ\Oꢋꢉ
EXWꢉꢃꢉ\QꢉꢄꢉRQH ꢊ,,Eꢋꢁꢁ<LHOGꢁꢋꢏ<ꢄꢁPSꢁꢇꢍ±ꢇꢀƒ&ꢊꢁ,5ꢁ
VSHFWUXPꢄꢁ ꢄꢁFP ꢓꢁꢂꢀꢃꢇꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁ ꢂꢀꢃꢇꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁSSPꢓꢁ
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FP ꢓꢁꢂꢀꢃꢇꢁꢈ& 2ꢉꢄꢁꢅꢂꢃꢆꢁꢈ& &ꢉꢊꢁ +ꢁ105ꢁVSHFWUXPꢄꢁ ꢄꢁ
SSPꢓꢁꢂꢊꢍꢍꢁVꢁꢈꢃ+ꢄꢁWꢌ%XꢉꢄꢁꢏꢊꢋꢀꢁGꢁꢈꢅ+ꢄꢁ+ ꢄꢁ-ꢁ ꢁꢏꢊꢐꢁ+]ꢉꢄꢁ
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