Bilitrienones from the chemical oxidation of dodecasubstituted porphyrins.

Tetrahedron
Owendi OngayiKevin M Smith

Abstract

The structure of the ring-opened product from direct oxidation of meso-tetraarylporphyrins has been controversial for three decades. Herein we show that bilitrienones 2 are obtained from oxidation of metal-free dodecasubstituted porphyrins 1 in the presence of sodium nitrite, trifluoroacetic acid and air oxygen. The presence of the para-nonyl groups in 1b stabilized the corresponding bilitrienone 2b, which was characterized by X-ray crystallography. In the absence of the para-nonyl groups bilitrienone 2a undergoes a rapid hydration reaction, giving biladienone 3a as the major isolated product. The molecular structures of 2b and 3a, and. the photochemical isomerization of 3a are discussed.

References

Jan 1, 1973·Journal of the Chemical Society. Perkin Transactions 1·J A Cavaleiro, K M Smith
Jan 1, 1972·Journal of the Chemical Society. Perkin Transactions 1·K M Smith
Oct 24, 1972·Biochemistry·M J BurkeA Moscowitz

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Citations

Mar 18, 2011·Inorganic Chemistry·Takahisa IkeueMikio Nakamura
Jul 12, 2016·Chemistry : a European Journal·Meenakshi SharmaChristian Brückner

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