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Cyclizations and intermolecular additions of alkoxycarbonyloxy radicals from N-hydroxypyridine-2-thione carbonates

✍ Scribed by Martin Newcomb; M Udaya Kumar; Jean Voivin; Elisabeth Crépon (née daSilva); Samir Z Zard

Book ID
104212804
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
320 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

Alkoxycarbonyloxy radicals from ally1 and homoallyl alcohols cyclize in an exe fashion to give, respectively, 3-substituted 1,Zdiol camonates and 4-substituted 1,3diol carbonates whereas simple alkoxycarbonyloxy radicals add intermolecularly to ethyl vinyl ether to give, ultimately, carbonates of glycolaldehyde derivatives.

📜 SIMILAR VOLUMES

N-Hydroxypyridine-2-thione carbamates. V
N-Hydroxypyridine-2-thione carbamates. VII. Intermolecular addition and addition-cyclization reactions of aminium cation radicals
✍ Martin Newcomb; M. Udaya Kumar 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 294 KB

Dialkylaminium cation radicals pmduced from the title precursors add to ethyl vinyl ether to give &amino ethers in good yields. When an ally1 group is present on nitrogen, a cyclization reaction follows the addition, and pyrrolidines ate formed. Simple cyclic enol ethers also can be employed.

Facile generation of dialkylaminyl radic
Facile generation of dialkylaminyl radicals from N-hydroxypyridine-2-thione carbamates. Application in kinetic studies of small ring cycloalkylaminyl radical ring openings
✍ Martin Newcomb; Park Seung-Un; Jere Kaplan; Donald J. Marquardt 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 251 KB

The preparation of N-hydroxypyridine-2-thione carbamates and the formation of dialkylaminyl radicals from these species are described, and the application of this methodology in kinetic studies of aminyl radical rearrangements is demonstrated. We have used aminyl radical rearrangements as probe rea

Rate constants and arrhenius function fo
Rate constants and arrhenius function for scavenging of octyl radical by an N-hydroxypyridine-2-thione ester
✍ Martin Newcomb; Jere Kaplan 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 256 KB

Rate constants for reactions of octyl radical with its N-hydroxypyridine-2-thione ester precursor were determined using the reduction of octyl radical by n-Bu SnH as a competition reaction. 3 The use of radical cyclization and functionalization steps in organic synthesis is becoming increasingly p