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1982•Collection of Czechoslovak Chemical CommunicationsRequires access

1,3-Dipolar cycloaddition of C-benzoyl-N-phenylnitrone with dihydrofuran derivatives. Investigation of endo-exo stereoselectivity

L. FISERA, Miloslava Dandárová, Jaroslav Kováč, Anton Gáplovský, Juraj Patúš, Igor Goljer

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Abstract

C-Benzoyl-N-phenylnitrone (Ia) reacts with dihydrofuran derivatives (2,3-dihydro- and 2,5-dihydrofuran, 2,5-dimethoxy- and 2,5-diacetoxy-2,5-dihydrofuran) via 1,3-dipolar cycloaddition to give diastereoisomeric pair of exo- and endo- cycloadducts. The endo-exo stereoselectivity of the reaction is discussed. Cycloaddition of C,N-diphenylnitrone (Ib) with 2,3-dihydrofuran is also described. The cycloaddition kinetics have been studied with the nitrone Ia and non-substituted dihydrofurans.

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What this paper is about

C-Benzoyl-N-phenylnitrone (Ia) reacts with dihydrofuran derivatives (2,3-dihydro- and 2,5-dihydrofuran, 2,5-dimethoxy- and 2,5-diacetoxy-2,5-dihydrofuran) via 1,3-dipolar cycloaddition to give diastereoisomeric pair of exo- and endo- cycloadducts. The endo-exo stereoselectivity of the reaction is discussed. Cycloaddition of C,N-diphenylnitrone (Ib) with 2,3-dihydrofuran is also described. The cycloaddition kinetics have been studied with the nitrone Ia and non-substituted dihydrofurans.

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Available abstract

C-Benzoyl-N-phenylnitrone (Ia) reacts with dihydrofuran derivatives (2,3-dihydro- and 2,5-dihydrofuran, 2,5-dimethoxy- and 2,5-diacetoxy-2,5-dihydrofuran) via 1,3-dipolar cycloaddition to give diastereoisomeric pair of exo- and endo- cycloadducts. The endo-exo stereoselectivity of the reaction is discussed. Cycloaddition of C,N-diphenylnitrone (Ib) with 2,3-dihydrofuran is also described. The cycloaddition kinetics have been studied with the nitrone Ia and non-substituted dihydrofurans.

Key concepts: Cycloaddition, Stereoselectivity, Nitrone, Chemistry, 1,3-Dipolar cycloaddition, Stereochemistry, Organic chemistry, Catalysis

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