1- ethoxyethyl carbamate

In this reaction, carbamate esters were obtained after long reaction times (70 h), in 0.06-11% yield, depending on the olefin/amine molar ratio (l-10mol/mol) and temperature (308-353 K). Since 1-ethoxyethyl carbamate was formed as the sole regio-isomer product, but there was no formation of the 2-ethoxyethyl ester, the reaction was believed to proceed by an electrophilic addition to the vinyl ether of carbamic acid, formed by reversible reaction of C02 with amine (see Equation 6.1). 

The carbamates 327 (R R2 Pr or Bu) react with t-butylthiol, malonic acid and ethoxyethylene under irradiation to yield the (ethoxyethyl)amines 333 via the radical cations 332. The A-allyl analogues 334 (R = Pr or PhCH2) cyclize to pyrrolidines 335382. 

The transfer of a carbamate moiety to olefins has been documented only in very few cases, using activated unsaturated substrates. For example, Yoshida and Inoue reported the selective (100%) formation of 1-ethoxyethyl N,N-dialkylcarbamate esters by the reaction of C02 (5 MPa) with ethyl vinyl ether and secondary amines R2NH (R = Me, Et) in the absence of any catalyst (Equation 6.11) [85]. 

C6H1203 2-ethoxyethyl acetate 111-15-9 -61.70 1.2330 2 8825 C6H13N02 tert-pentyl carbamate 590-60-3 24.32 1.0011 2... 

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