Tetrahedron Letters p. 7989 - 7992 (1994)
Update date:2022-08-04
Topics:
Samizu, Kiyohiro
Ogasawara, Kunio
Birch reduction of several 5-aryl-4,5-dihydro-1,3-dioxepins gave rise to 3-arylbutanal in moderate to good yields by hydrogenolytic cleavage of the homobenzylic-homoallylic carbon-oxygen bond when the benzylic-allylic carbon is tertiary.However, the reaction did not take place when the benzylic-allylic carbon is quaternary.Moreover, the reaction was found to proceed with complete racemization at the benylic-allylic center indicating a concurrent elimination-reduction pathway to be involved.
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