- The photochemical rearrangement of 1,2-dihydronaphthalenes into 1,4-dihydronaphthalenes induced by amines
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The synthetic usefulness of the deprotonation/protonation reaction of excited 1,2-dihydronaphthalenes into 1,4-dihydronaphthalenes induced by amines has been investigated using 13 different substituted 1,2-dihydronaphthalenes and related compounds.The yield of the rearrangement ranges from 5 to 96percent.The formation of side-products depends on the position of protons in the substrate, which can be abstracted by the amine, and on competitive photoreactions.
- Cuppen, Th. J. H. M.,Berendsen, N.,Laarhoven, W. H.
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p. 168 - 171
(2007/10/02)
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- Photochemistry of 3-methyl-1,2-dihydronaphthalene
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Irradiation of the title compound (6) with a broad spectrum lamp at room temperature afforded 2-methylidene-1,2,3,4-tetrahydronaphthalene(8) and 2-methylnaphthalene (7).Apart from 8, irradiation of 6 at -45 deg also afforded 5-methylbenzobicyclohex-2-ene (12) 1-methylidene-2-(2-tolyl)cyclopropane (13) as well as a small amount of 2-methyl-1,4-dihydronaphthalene (14).Both 12 and 13 originate from the ring-opened product of 6.Compound 14 is probably formed via a retro di-?-methane rearrangement from 12.Irradiation of 6 in n-propylamine afford the same photoproducts, 14 being the main one in this case.
- Laarhoven, W. H.,Berendsen, N.
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p. 367 - 371
(2007/10/02)
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