Peri‐selective photocycloadditions of methyl 2‐pyrone‐5‐carboxylate with unsaturated cyclic ethers | Zendy

Shimo Tetsuro | Zendy; Iwakiri Tsuneaki | Zendy; Somekawa Kenichi | Zendy; Suishu Takaaki | Zendy

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Peri‐selective photocycloadditions of methyl 2‐pyrone‐5‐carboxylate with unsaturated cyclic ethers

Author(s) -

Shimo Tetsuro,

Iwakiri Tsuneaki,

Somekawa Kenichi,

Suishu Takaaki

Publication year - 1992

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570290136

Subject(s) - chemistry , cycloaddition , mndo , carboxylate , adduct , medicinal chemistry , excited state , stereochemistry , organic chemistry , molecule , catalysis , physics , nuclear physics

Photosensitized cycloaddition reaction of methyl 2‐pyrone‐5‐carboxylate ( 1 ) with 2,3‐dihydrofuran gave cis‐ exo‐ and cis ‐endo‐[2 + 2] cycloadducts across the C 3 ‐C 4 double bond in 1 , and a [4 + 2] cycloadduct which was different in addition‐orientation from the Diels‐Alder adducts. Each [2 + 2] cycloadduct was obtained by the use of sensitizers having different triplet energies. Photosensitized reactions of 1 with 3,4‐dihydro‐2 H ‐pyrans afforded cis ‐endo‐[2 + 2] cycloadducts, respectively. The photocycloaddition mechanism was also explained from the excited state of 1 calculated by means of MNDO‐Cl method.

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