Synthesis and Properties of Azoles and Their Derivatives : XLIII. Regio- and Stereoselectivity of [2+3] Cycloaddition Reaction of E-B-Nitrostyrene to Z-C-Aryl-N-phenylnitrones

• Autorzy: Barański A.
• Języki publikacji: EN

Abstrakty

EN

E-B-Nitrostyrene (1) reacts with Z-C-acryl- N-phenylnitrones (2a-h) exclusively to give trans- and cis-2,5-diphenyl-3-aryl-4-nitroisoxazolidines (3a-h, 4a-h) in high yield. The molar ratio of trans and cis stereoisomers is affected by substituent in phenyl ring of the parent nitrone (2c). The reaction is found by AM1 calculations to be controlled bt the interactions of the HOMO of nitrone with the LUMO of nitrostyrene.

Słowa kluczowe

EN

nitrones; nitroalkenes; [2+3] cycloaddition; regioselectivity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2000
• Tom: Vol. 74, nr 6
• Strony: 767--775

Twórcy

autor

Barański A.

• Institute of Organic Chemistry and Technology Technical University 31-155 Kraków Warszawska 24, Poland