2(3H)- and 2(5H)-Furanones. IV. The Di-π-methane Rearrangement of 3, 4-Bis(phenymethyl)-2(5H)-furanone

Takefumi MOMOSE; Genzoh TANABE; Hisayuki TSUJIMORI; Osamu MURAOKA

doi:10.1248/cpb.40.2525

Takefumi MOMOSE, Genzoh TANABE, Hisayuki TSUJIMORI, Osamu MURAOKA

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Keywords: 3, 4-bis(phenylmethyl)-2(5H)-furanone, photo-reaction, de-π-methane rearrangement, β-apolignan, 3-oxabicy-clo[3.1.0]hexan-2-one, hydrogenolysis

JOURNAL FREE ACCESS

1992 Volume 40 Issue 9 Pages 2525-2530

DOI https://doi.org/10.1248/cpb.40.2525

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Abstract

The photo-irradiation of 3, 4-bis(phenylmethyl)-2(5H)-furanone (5) in acetone or in methanol resulted in selective rearrangement of the 4-phenymethyl moiety and gave 5-phenyl-1-(phenylmethyl)-3-oxabocyclo[3.1.0]hexan-2-one (9)along with cis- and trans-3, 4-bis(phenylmethyl)dihydro-2(3H)-furanone (10a and 10b). The difference in photochemical behavior from that of β-apolignan (1) is discussed.

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