Synthesis of 2-(Phenylselanyl)tetrahydrofurans from γ-Lactones and of γ-Hydroxydiselenoacetals from γ-Lactols

Abstract

A known one-pot procedure for the synthesis of 2-(phenylselanyl)tetrahydrofurans could be applied to the transformation of γ-lactones 3a-c into 2-(phenylselanyl)tetrahydrofurans 1a-c. Surprisingly, formation of γ-hydroxydiselenoacetals 5b and 5c was observed when γ-lactols 4b and 4c were treated with selenophenol and boron trifluoride etherate.

Key words

furans - lactones - reductions - selenium - selenoacetal

References

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6

In ref. 7 only a 90 MHz ¹H NMR spectrum of 1c was reported. We present data resulting from a 300 MHz spectrum and a ¹³C NMR spectrum. Comparing our data with many other 1,5-disubstituted tetrahydrofuran derivatives, a cis-configuration of the major isomer is very likely.