Alkoxycarbonylation of Alcohols and Phenols by Nitrosoformates

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Title:Alkoxycarbonylation of Alcohols and Phenols by Nitrosoformates
Creators:
Mindl, Jaromír
Halama, Aleš
Černošek, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 7, pp. 1053-1063
Uncontrolled Keywords:Alcohols, alkoxycarbonylation, Lead dioxide, hydroxycarbamates oxidation, Phenols, alkoxycarbonylation, Carbonates, preparation by alkoxycarbonylation

Abstract

Unstable neutral radicals [ROCONHOU<sup>.</sup>] <strong>2</strong> and nitrosoformates <strong>3</strong> are formed by oxidation of <i>N</i>-hydroxycarbamates with lead dioxide. In the presence of alcohols or phenols and water they solvolyzed to mixtures of symmetrical <strong>4</strong> and asymmetrical <strong>5</strong> carbonates. The content of asymmetrical carbonates <strong>5</strong> increases with increasing reactivity of the nitrosoformates <strong>3</strong> formed, temperature, the content of water in the reaction mixture, and with decreasing reactivity of alcohol. The reactivities of individual alcohols have been evaluated with the help of competitive alcoholysis. The new method of alcohol or phenol alkoxylation has been verified experimentally by preparing six asymmetrical carbonates which were obtained in 34 to 47% yields.

Title:Alkoxycarbonylation of Alcohols and Phenols by Nitrosoformates
Creators:
Mindl, Jaromír
Halama, Aleš
Černošek, Zdeněk
Uncontrolled Keywords:Alcohols, alkoxycarbonylation, Lead dioxide, hydroxycarbamates oxidation, Phenols, alkoxycarbonylation, Carbonates, preparation by alkoxycarbonylation
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:7
Page Range:pp. 1053-1063
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961053UNSPECIFIED
ID Code:1009
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Mindl, Jaromír; Halama, Aleš; Černošek, Zdeněk (1996) Alkoxycarbonylation of Alcohols and Phenols by Nitrosoformates. Collection of Czechoslovak Chemical Communications, 61 (7). pp. 1053-1063. ISSN 0010-0765

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