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Photochemical rearrangements of cross-conjugated cyclohexadienones. Formation of spiro [4.5] dec-3-en-2-ones.

✍ Scribed by Paul J. Kropp; William F. Erman

Book ID: 104241765
Publisher: Elsevier Science
Year: 1963
Tongue: French
Weight: 237 KB
Volume: 4
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)90570-2

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✦ Synopsis

IT is well established that 4-ntethylcyclohexadienones of the santonin type undergo photochemical transformation in aqueous acetic acid to perhydroasulene derivatives of the isophotosantonic la&one type.' The photochemical properties of cyclohexadienones which are unsubstituted at C4 have also been studied, but the rearrangement products have not been well characterized2 We wish to report that dienones of this type have been found to undergo photochemical transformation in acidic media to Spiro p.57 dec-3-en-e-one derivatives. IrrediaUon3 of 4aS,~-d~thy1-5,6,7,8-tetrahydro-2(4aR)-naphtha1enone (I)~ in 45s acetic acid at 20' gave the spiro ketone II, m.p. 98-yy", in 16$ yield. When

Cf., P. de Mayo and S. T. Reid, Quwt. Rev. (London) l&393 (1961).

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