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Photoinduced addition of nucleophiles to bicyclo[2.2.1]hepta-2,5-diene

✍ Scribed by Paul G. Gassman; Kurt D. Olson

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
251 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The l-cyanonaphthalene photosensitized addition of water and methanol to the cation-radical of bicyclo[2.2.1]hepta-2,5-diene is described.

Recently, we demonstrated that nucleophiles could be added across strained carbon-carbon sigma bonds in photosensitized reactions which are readily interpreted in terms of the initial transfer of an electron from the strained sigma bond to the excited state of photosensitizers such as 1-cyanonaphthalene (l-CN).*

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Die elektronische Wechselwirkung zwischen einem p-Orbital in eines Bicyclo[2.2.1]heptadiensystems und den n-Orbitalen der durch den Raum zeigt sich besonders an der auBergew8hnlichen r3i der 7-Stellung Doppelbindungen StabilitZt des No. 24 Anmerkunqen und Literatur [: 'I c 11 c 21 c 31