Chemistry of four-membered cyclic nitrones. 3. Reaction with nucleophilic reagents and stereospecific conversion into 1-hydroxyazetidines
…, S Harkema, GJ Van Hummel
Index: Pennings, Marcel L.M.; Reinhoudt, David N.; Harkema, Sybolt; Hummel, Gerrit J. van Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4419 - 4425
Full Text: HTML
Citation Number: 12
Abstract
Four-membered cyclic nitrones (1) react with a variety of nucleophiles (MeMgI, CN-, OH-, MeO-, and H-) by stereospecific addition to the C= N bond. Reaction of la with potassium cyanide and with methylmagnesium iodide yields the 1-hydroxyazetidines 2a and 2b, respectively. Reduction of lb with lithium aluminum hydride and with sodium borohydride affords the 1-hydroxyazetidine derivatives 3 and 4, respectively. Sodium hydroxide in ...
Related Articles:
[Hansen, John F.; Kim, Yong In; McCrotty, Stephen E.; Strong, Scott A.; Zimmer, Douglas E. Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 475 - 479]
Application of [3+ 2]-Cycloaddition in the Synthesis of Valdecoxib
[Reddy, Anumula Raghupathi; Goverdhan, Gilla; Sampath, Aalla; Mukkanti, Khagga; Reddy, Padi Pratap; Bandichhor, Rakeshwar Synthetic Communications, 2012 , vol. 42, # 5 p. 639 - 649]
[Hansen, John F.; Kim, Yong In; McCrotty, Stephen E.; Strong, Scott A.; Zimmer, Douglas E. Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 475 - 479]
Application of [3+ 2]-Cycloaddition in the Synthesis of Valdecoxib
[Reddy, Anumula Raghupathi; Goverdhan, Gilla; Sampath, Aalla; Mukkanti, Khagga; Reddy, Padi Pratap; Bandichhor, Rakeshwar Synthetic Communications, 2012 , vol. 42, # 5 p. 639 - 649]
Application of [3+ 2]-Cycloaddition in the Synthesis of Valdecoxib
[Reddy, Anumula Raghupathi; Goverdhan, Gilla; Sampath, Aalla; Mukkanti, Khagga; Reddy, Padi Pratap; Bandichhor, Rakeshwar Synthetic Communications, 2012 , vol. 42, # 5 p. 639 - 649]