A Novel Photochemical Reaction of 2-Alkoxynicotinates to Cage-Type Photodimers

Masami Sakamoto, Tadao Yagi, Shohei Fujita, Takashi Mino, Takashi Karatsu, Tsutomu Fujita

The Journal of Organic Chemistry · 2002 · 11 citations · 20 references

Concepts

Abstract

Irradiation of a benzene solution of 2-alkoxynicotinic acid alkyl esters gave cage-type photodimers in good yields, the structure of which was established by X-ray single-crystal analysis. The maximum quantum yield was 8.0 x 10(-)(2) when a 5.0 M (almost neat) solution was used. Photolysis of phenyl 2-methoxynicotinate promoted photo-Fries rearrangement to give 1,3- and 1,5-rearranged products. Excimer emission of methyl 2-methoxynicotinate was observed at 77 K.

References

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