Synthesis of o-nitrosoacylbenzenes from o-nitrobenzyl alcohols and their derivatives

Article abstract of DOI:10.1134/S1070428006010143

Nitration of substituted benzyl alcohols, as well as ethers and esters derived therefrom, with nitric acid in acetic anhydride was studied. The corresponding o-nitrobenzyl alcohols and their derivatives formed as the primary products are capable of being converted into o-nitrosoacylbenzenes by the action of acids. Pleiades Publishing, Inc., 2006.

Full text of DOI:10.1134/S1070428006010143

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ꢄꢆꢇꢂꢊꢌꢆꢈꢃꢋꢅꢂꢃꢑꢄꢂꢊꢃꢆꢆꢋꢅꢂꢃꢁꢐꢂꢊꢌꢑꢈꢀꢋꢅꢂꢃꢏꢆꢂꢊꢄꢃꢈꢌꢋꢅꢂꢃꢇꢁꢂ
&+&+ ꢋꢅꢂꢁꢈꢐꢄꢂGꢂꢊꢄ+ꢅꢂ+ ꢅꢂ- ꢂ ꢂꢀꢈꢀꢂ+]ꢋꢅꢂꢀꢈꢄꢄꢂGꢂꢊꢄ+ꢅꢂ ꢊꢌꢌꢈꢆꢋꢅꢂꢃꢌꢃꢂꢊꢌꢇꢈꢑꢋꢅꢂꢃꢃꢐꢂꢊꢌꢑꢈꢁꢋꢅꢂꢃꢆꢌꢂꢊꢄꢑꢈꢃꢋꢅꢂꢑꢃꢂꢊꢇꢆꢈꢀꢋꢅꢂꢁꢁꢂ
ꢅꢂ- ꢂ ꢂꢀꢈꢀꢂ+]ꢋꢈꢂ0DVVꢂVSHFWUXPꢅꢂPꢎ]ꢂꢊ, ꢅꢂIꢋꢍꢂꢄꢆꢑꢂ ꢊꢇꢐꢈꢏꢋꢅꢂꢐꢁꢂꢊꢑꢇꢈꢃꢋꢈꢂ
&+&+ ꢅꢂ-ꢂ ꢂꢏꢈꢄꢂ+]ꢋꢅꢂꢄꢈꢃꢄꢂVꢂꢊꢌ+ꢅꢂ&2&+ ꢋꢅꢂꢐꢈꢑꢄꢂTꢂꢊꢃ+ꢅꢂ
+
ꢊꢇꢈꢃꢋꢂ>0@ ꢅꢂꢃꢏꢁꢂꢊꢐꢆꢈꢄꢋꢅꢂꢃꢐꢆꢂꢊꢃꢌꢈꢑꢋꢅꢂꢃꢃꢑꢂꢊꢃꢇꢈꢁꢋꢅꢂꢃꢆꢌꢂ
ꢊꢄꢇꢈꢁꢋꢅꢂꢑꢃꢂꢊꢄꢄꢈꢃꢋꢅꢂꢁꢁꢂꢊꢄꢇꢈꢀꢋꢅꢂꢏꢌꢂꢊꢇꢈꢇꢋꢅꢂꢐꢃꢂꢊꢑꢈꢁꢋꢅꢂꢇꢌꢂꢊꢃꢆꢆꢋꢈꢂ
)RXQGꢅꢂIꢍꢂ&ꢂꢐꢏꢈꢑꢀꢅꢂꢐꢁꢈꢆꢇꢒꢂ+ꢂꢐꢈꢃꢃꢅꢂꢐꢈꢃꢄꢅꢂ1ꢂꢏꢈꢌꢄꢅꢂꢏꢈꢇꢃꢈꢂ
& + 12 ꢈꢂ&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢐꢁꢈꢇꢃꢒꢂ1ꢂꢐꢈꢌꢆꢒꢂ1ꢂꢏꢈꢁꢆꢈꢂ
7KHꢂ QLWUDWLRQꢂ RIꢂ ꢑꢈꢏꢂ Jꢂ ꢊꢆꢈꢆꢐꢂ PROꢋꢂ RIꢂ DOFRKROꢂ ,;ꢅꢂ
IROORZHGꢂ E\ꢂ VHSDUDWLRQꢂ RIꢂ WKHꢂ SURGXFWꢂ PL[WXUHꢂ E\ꢂ
ꢓꢂ &DOFXODWHGꢂRQꢂWKHꢂUHDFWHGꢂDOFRKROꢂ9ꢈꢂ
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FROXPQꢂ FKURPDWRJUDSK\ꢂ RQꢂ VLOLFDꢂ JHOꢂ ꢊꢇꢆ±ꢃꢆꢆꢂ Pꢋꢂ ꢇꢈꢆꢃꢒꢂ1ꢂꢑꢈꢏꢌꢅꢂꢑꢈꢁꢑꢈꢂ& + 1 2 ꢈꢂ&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢇꢏꢈꢇꢀꢒꢂ
XVLQJꢂ GLHWK\Oꢂ HWKHU±OLJKWꢂ SHWUROHXPꢂ HWKHUꢂ ꢊꢃꢍꢃꢆꢋꢂ DVꢂ +ꢂꢇꢈꢄꢏꢒꢂ1ꢂꢑꢈꢀꢏꢒꢂꢂ
HOXHQWꢅꢂJDYHꢂꢁꢈꢇꢁꢂJꢂꢊꢐꢌIꢋꢂRIꢂQLWUDWHꢂ;9ꢅꢂꢌꢈꢏꢁꢂJꢂꢊꢄꢏIꢋꢂ
RIꢂQLWUDWHꢂ;9,ꢅꢂꢆꢈꢀꢃꢂJꢂꢊꢑIꢋꢂRIꢂꢃꢉWHUWꢉEXW\OꢉꢇꢉQLWUREHQꢉ
]HQHꢂꢊ9,,ꢋꢂꢊLGHQWLILHGꢂE\ꢂFRPSDULQJꢂZLWKꢂDQꢂDXWKHQWLFꢂ
VDPSOHꢋꢅꢂDQGꢂꢆꢈꢐꢇꢂJꢂꢊꢇIꢋꢂRIꢂDFHWDWHꢂ;9,,ꢈꢂ
ꢅꢀꢑꢈꢃꢉꢀ(WK\OHQHGLR[\ꢀꢆꢀQLWURSKHQ\OꢐSURS\Oꢁ
DFHWDWHꢁ ꢑ;;,ꢐꢂꢂPSꢂꢀꢆ±ꢀꢃƒ&ꢈꢂ,5ꢂVSHFWUXPꢅꢂ ꢅꢂFP ꢍꢂ
ꢃꢌꢁꢆꢅꢂꢃꢐꢌꢆꢂꢊ12 ꢋꢒꢂꢃꢁꢌꢐꢂꢊ&2ꢋꢈꢂ +ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂ
SSPꢍꢂꢃꢈꢆꢀꢂWꢂꢊꢌ+ꢅꢂ&+&+ &+ ꢋꢅꢂꢃꢈꢑꢄꢂPꢂDQGꢂꢃꢈꢑꢁꢂPꢂꢂ
ꢅꢀꢑꢈꢀWHUWꢀ%XW\OꢀꢇꢀQLWURSKHQ\OꢐSURS\Oꢁ QLWUDWHꢁ
ꢊꢃ+ꢂHDFKꢅꢂ&+&+ &+ ꢋꢅꢂꢄꢈꢃꢃꢂVꢂꢊꢌ+ꢅꢂ&+ &2ꢋꢅꢂꢇꢈꢌꢆꢂPꢂ
ꢑ;9ꢐꢂꢂ 9LVFRXVꢂ RLO\ꢂ VXEVWDQFHꢈꢂ +ꢂ 105ꢂ VSHFWUXPꢅꢂ ꢅꢂ DQGꢂꢇꢈꢌꢀꢂPꢂꢊꢄ+ꢂHDFKꢅꢂ2&+ &+ 2ꢋꢅꢂꢏꢈꢄꢇꢂGꢈGꢂꢊꢃ+ꢅꢂ
SSPꢍꢂꢃꢈꢆꢃꢂWꢂꢊꢌ+ꢅꢂ&+ &+ ꢋꢅꢂꢃꢈꢇꢃꢂVꢂꢊꢑ+ꢅꢂWꢉ%XꢋꢅꢂꢃꢈꢀꢁꢂPꢂ &+&+ &+ ꢋꢅꢂꢁꢈꢆꢃꢂVꢂꢊꢃ+ꢅꢂꢏꢉ+ꢋꢅꢂꢁꢈꢏꢌꢂVꢂꢊꢃ+ꢅꢂꢌꢉ+ꢋꢈꢂ
)RXQGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢏꢁꢅꢂꢐꢐꢈꢐꢄꢒꢂ+ꢂꢐꢈꢐꢐꢅꢂꢐꢈꢏꢃꢒꢂ1ꢂꢇꢈꢁꢃꢅꢂꢇꢈꢏꢃꢈꢂ
& + 12 ꢈꢂ&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢐꢃꢒꢂ+ꢂꢐꢈꢌꢁꢒꢂ1ꢂꢇꢈꢑꢀꢒꢂꢂ
DQGꢂ ꢄꢈ ꢆꢄꢂ Pꢂ ꢊꢃ+ꢂ HDFKꢅꢂ &+&+ &+ ꢋꢅꢂ ꢐꢈ ꢏꢀꢂ Wꢂ ꢊꢃ+ꢅꢂ
&+&+ &+ ꢋꢅꢂꢁꢈꢌꢃꢂGꢂꢊꢃ+ꢅꢂ+ ꢅꢂ- ꢂ ꢂꢄꢈꢆꢂ+]ꢋꢅꢂꢁꢈꢇꢌꢂGꢈGꢂ
ꢊꢃ+ꢅꢂ+ ꢅꢂ- ꢂ ꢂꢄꢈꢆꢅꢂ- ꢂ ꢂꢀꢈꢏꢂ+]ꢋꢅꢂꢁꢈꢐꢑꢂGꢂꢊꢃ+ꢅꢂ+ ꢅꢂꢂ
- ꢂ ꢂꢀꢈꢏꢂ+]ꢋꢈꢂ)RXQGꢅꢂIꢍꢂ&ꢂꢐꢇꢈꢑꢀꢅꢂꢐꢐꢈꢃꢄꢒꢂ+ꢂꢏꢈꢄꢃꢅꢂꢏꢈꢄꢏꢒꢂ
1ꢂꢑꢈꢇꢁꢅꢂꢑꢈꢐꢐꢈꢂ& + 1 2 ꢈꢂ&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢌꢃꢒꢂꢂ
+ꢂꢏꢈꢇꢌꢒꢂ1ꢂꢑꢈꢑꢌꢒꢂꢂ
ꢅꢀꢑꢈꢃꢉꢀ(WK\OHQHGLR[\ꢀꢆꢀQLWURSKHQ\OꢐSURSDQROꢁ
ꢑ;,;ꢐꢂꢂPSꢂꢃꢐꢏ±ꢃꢐꢁƒ&ꢈꢂ,5ꢂVSHFWUXPꢅꢂ ꢅꢂFP ꢍꢂꢃꢌꢀꢆꢅꢂ
ꢃꢐꢌꢄꢂꢊ12 ꢋꢒꢂꢌꢄꢏꢆꢂꢊ2+ꢋꢈꢂ +ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂSSPꢍꢂ
ꢆꢈꢑꢏꢂWꢂꢊꢌ+ꢅꢂ&+&+ &+ ꢋꢅꢂꢃꢈꢇꢀꢂPꢂDQGꢂꢃꢈꢏꢏꢂPꢂꢊꢃ+ꢂHDFKꢅꢂ
&+&+ &+ ꢋꢅꢂꢇꢈꢌꢄꢂPꢂꢊꢇ+ꢅꢂ2&+ &+ 2ꢋꢅꢂꢐꢈꢆꢃꢂPꢂꢊꢃ+ꢅꢂ
&+&+ &+ ꢋꢅꢂꢐꢈꢃꢇꢂEUꢈVꢂꢊꢃ+ꢅꢂ2+ꢋꢅꢂꢁꢈꢄꢃꢂVꢂꢊꢃ+ꢅꢂꢏꢉ+ꢋꢅꢂ
ꢁꢈꢇꢀꢂVꢂꢊꢃ+ꢅꢂꢌꢉ+ꢋꢈꢂ)RXQGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢌꢄꢅꢂꢐꢐꢈꢇꢃꢒꢂ+ꢂꢐꢈꢌꢃꢅꢂ
ꢐꢈꢄꢑꢒꢂ1ꢂꢐꢈꢇꢃꢅꢂꢐꢈꢏꢐꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢄꢄꢒꢂ
+ꢂꢐꢈꢇꢁꢒꢂ1ꢂꢐꢈꢀꢐꢈꢂ
ꢅꢀꢑꢈꢀWHUWꢀ%XW\OꢀꢆꢀQLWURSKHQ\OꢐSURS\Oꢁ QLWUDWHꢁ
ꢑ;9,ꢐꢂꢂ9LVFRXVꢂRLO\ꢂVXEVWDQFHꢈꢂ +ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂ
SSPꢍꢂꢃꢈꢃꢇꢂWꢂꢊꢌ+ꢅꢂ&+ &+ ꢋꢅꢂꢃꢈꢌꢁꢂVꢂꢊꢑ+ꢅꢂWꢉ%XꢋꢅꢂꢃꢈꢑꢁꢂPꢂ
DQGꢂ ꢄꢈꢆꢁꢂ Pꢂ ꢊꢃ+ꢂ HDFKꢅꢂ &+&+ &+ ꢋꢅꢂ ꢏꢈꢌꢁꢂ GꢈGꢂ ꢊꢃ+ꢅꢂ
&+&+ &+ ꢅꢂ- ꢂ ꢂꢑꢈꢆꢅꢂ- ꢂ ꢂꢇꢈꢀꢂ+]ꢋꢅꢂꢁꢈꢐꢐꢂGꢂꢊꢃ+ꢅꢂ+ ꢅꢂ
- ꢂ ꢂ ꢀꢈ ꢄꢂ +]ꢋꢅꢂ ꢁꢈ ꢁꢆꢂ Gꢈ Gꢂ ꢊꢃ+ꢅꢂ + ꢅꢂ - ꢂ ꢂ ꢄꢈ ꢄꢅꢂ - ꢂ ꢂꢂ
ꢀꢈꢄꢂ +]ꢋꢅꢂ ꢀꢈꢆꢐꢂGꢂ ꢊꢃ+ꢅꢂ + ꢅꢂ - ꢂ ꢂꢄꢈꢄꢂ +]ꢋꢈꢂ )RXQGꢅꢂIꢍꢂꢂ
&ꢂꢐꢇꢈꢀꢄꢅꢂꢐꢐꢈꢆꢃꢒꢂ+ꢂꢏꢈꢃꢑꢅꢂꢏꢈꢄꢑꢒꢂ1ꢂꢑꢈꢐꢇꢅꢂꢑꢈꢐꢑꢈꢂ& + 1 2 ꢈꢂ
&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢐꢐꢈꢌꢃꢒꢂ+ꢂꢏꢈꢇꢌꢒꢂ1ꢂꢑꢈꢑꢌꢒꢂꢂ
7KHꢂQLWUDWLRQꢂRIꢂꢏꢈꢆꢐꢂJꢂꢊꢆꢈꢆꢄꢐꢂPROꢋꢂRIꢂDOFRKROꢂ
;;,;ꢅꢂ IROORZHGꢂ E\ꢂ FKURPDWRJUDSKLFꢂ VHSDUDWLRQꢂ RQꢂꢂ
DQꢂ$O 2 ꢂSODWHꢂꢊDFWLYLW\ꢂJUDGHꢂ,,ꢒꢂEHQ]HQHꢋꢅꢂJDYHꢂꢆꢈꢑꢐꢂJꢂ
ꢊꢄꢃIꢋꢂ RIꢂ ꢃꢅꢄꢉHWK\OHQHGLR[\ꢉꢇꢉQLWUREHQ]HQHꢂ ꢊ;;,,ꢋꢅꢂ
PSꢂꢃꢃꢑƒ&ꢂ>ꢃꢏ@ꢅꢂꢄꢈꢃꢂJꢂꢊꢌꢃIꢋꢂRIꢂFRPSRXQGꢂ;;;ꢅꢂDQGꢂ
ꢄꢈꢇꢂJꢂꢊꢌꢀIꢋꢂRIꢂEHQ]LVR[D]ROHꢂ;;;,ꢈꢂ
ꢅꢀꢑꢈꢀWHUWꢀ%XW\OꢀꢆꢀQLWURSKHQ\OꢐSURS\Oꢁ DFHWDWHꢁ
ꢑ;9,,ꢐꢂꢂ9LVFRXVꢂRLO\ꢂVXEVWDQFHꢈꢂ +ꢂ105ꢂVSHFWUXPꢅꢂ ꢅꢂ
SSPꢍꢂꢃꢈꢆꢌꢂWꢂꢊꢌ+ꢅꢂ&+ &+ ꢋꢅꢂꢃꢈꢌꢄꢂVꢂꢊꢑ+ꢅꢂWꢉ%XꢋꢅꢂꢃꢈꢀꢏꢂPꢂ
DQGꢂꢃꢈ ꢑꢑꢂ Pꢂ ꢊꢃ+ꢂ HDFKꢅꢂ&+&+ &+ ꢋꢅꢂꢄꢈꢄꢄꢂVꢂꢊꢌ+ꢅꢂ
&+ &2ꢋꢅꢂꢏꢈꢃꢐꢂGꢈGꢂꢊꢃ+ꢅꢂ&+&+ &+ ꢅꢂ- ꢂ ꢂꢁꢈꢏꢅꢂ- ꢂ ꢂꢂ
ꢇꢈꢆꢂ+]ꢋꢅꢂꢁꢈꢐꢃꢂGꢂꢊꢃ+ꢅꢂ+ ꢅꢂ- ꢂ ꢂꢀꢈꢄꢂ+]ꢋꢅꢂꢁꢈꢏꢄꢂGꢈGꢂꢊꢃ+ꢅꢂ
ꢈꢃꢉꢀ(WK\OHQHGLR[\ꢀꢆꢀQLWURVREHQ]RSKHQRQHꢁ
ꢑ;;;ꢐꢂꢂ'DUNꢂJUHHQꢂFU\VWDOVꢅꢂPSꢂꢃꢇꢆ±ꢃꢇꢃƒ&ꢈꢂ +ꢂ105ꢂ
VSHFWUXPꢅꢂ ꢅꢂSSPꢍꢂꢇꢈꢌꢀꢂPꢂꢊꢇ+ꢅꢂ2&+ &+ 2ꢋꢅꢂꢁꢈꢆꢄꢂVꢂ
ꢊꢃ+ꢅꢂꢌꢉ+ꢋꢅꢂꢁꢈꢆꢑꢂVꢂꢊꢃ+ꢅꢂꢏꢉ+ꢋꢅꢂꢁꢈꢇꢃꢂWꢂꢊꢄ+ꢅꢂꢌꢔꢉ+ꢅꢂꢐꢔꢉ+ꢋꢅꢂ
ꢁꢈꢐꢇꢂWꢂꢊꢃ+ꢅꢂꢇꢔꢉ+ꢋꢅꢂꢁꢈꢁꢀꢂGꢂꢊꢄ+ꢅꢂꢄꢔꢉ+ꢅꢂꢏꢔꢉ+ꢋꢈꢂ)RXQGꢅꢂIꢍꢂꢂ
&ꢂꢏꢏꢈꢇꢑꢅꢂꢏꢏꢈꢐꢏꢒꢂ+ꢂꢇꢈꢆꢆꢅꢂꢇꢈꢆꢌꢒꢂ1ꢂꢇꢈꢑꢇꢅꢂꢇꢈꢑꢏꢈꢂ& + 12 ꢈꢂ
&DOFXODWHGꢅꢂIꢍꢂ&ꢂꢏꢏꢈꢑꢃꢒꢂ+ꢂꢇꢈꢃꢄꢒꢂ1ꢂꢐꢈꢄꢆꢒꢂꢂ
+
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