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The chromous chloride promoted addition of N-chlorocarbamates to olefins the synthesis of β-chlorocarbamates

✍ Scribed by J. Lessard; J.M. Paton

Book ID
104229858
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
192 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis

B-chlorocarbamates have previously been prepared from olefins by thermal addition of N,Ndichlorourethane (1,2,3) and by photochemical addition of N-chlorourethane (NCU) (3 a-c, 4). We discovered a convenient way of adding various N-chlorocarbamates to olefins in very good yields using chromous chloride as the promoting agent. This new reaction constitutes a novel use for the chromous ion and appears to be of theoretical and synthetic importance.

The reaction with cyclohexene is illustrated in Scheme I. The general procedure is as ROCONHCl + (j CrC12 3 aITR + oNHCooR + m+ ROCONHZ

📜 SIMILAR VOLUMES

The chromous chloride promoted addition
The chromous chloride promoted addition of N-chlorocarbamates to enol ethers the synthesis of N-alkoxycarbonyl derivatives of 2-amino sugars and of α-amino ketones and aldehydes
✍ J. Lessard; H. Driguez; J.P. Vermes 📂 Article 📅 1970 🏛 Elsevier Science 🌐 French ⚖ 222 KB

In the preceding communication (l),we describe a new reaction which utilises chromous chloride to promote the addition of N-chlorocarbamates to olefins in good yjelds. We have applied this reaction to four enol ethers which illustrate the synthetic importance of the novel reaction. Dihydropyran. -N