TY - JOUR
T1 - Tris(bipyridyl)ruthenium(ii)-photosensitized reaction of 1-benzyl-1,4-dihydronicotinamide with benzyl bromide
AU - Hironaka, Katsuhiko
AU - Fukuzumi, Shunichi
AU - Tanaka, Toshio
PY - 1984
Y1 - 1984
N2 - An NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH), reduces benzyl bromide to yield toluene as the main product under irradiation of the absorption band of BNAH in the presence of pyridine in acetonitrile, while the addition of a sensitizer tris(bipyridyl)ruthenium(II) {[Ru(bpy)3]2+} to the BNAH-benzyl bromide system results in a drastic change in the photoreduced products, yielding 1,2-diphenylethane as the main product. Photosensitization by [Ru(bpy)3]2+has been shown to change the mechanism of the photochemical reaction of BNAH with benzyl bromide; reaction in the absence of [Ru(bpy)3]2+proceeds by a radical chain mechanism involving benzyl radicals as the chain carrier which is formed by electron transfer from the excited state of BNAH to benzyl bromide. However, the [Ru(bpy)3]2+-mediated photoreduction of benzyl bromide with BNAH occurs in the presence of [Ru(bpy)3]2+, where benzyl bromide is subject to two-electron reduction by [Ru(bpy)3]+which is formed by an electron transfer from BNAH to the excited state of [Ru(bpy)3]2+.
AB - An NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH), reduces benzyl bromide to yield toluene as the main product under irradiation of the absorption band of BNAH in the presence of pyridine in acetonitrile, while the addition of a sensitizer tris(bipyridyl)ruthenium(II) {[Ru(bpy)3]2+} to the BNAH-benzyl bromide system results in a drastic change in the photoreduced products, yielding 1,2-diphenylethane as the main product. Photosensitization by [Ru(bpy)3]2+has been shown to change the mechanism of the photochemical reaction of BNAH with benzyl bromide; reaction in the absence of [Ru(bpy)3]2+proceeds by a radical chain mechanism involving benzyl radicals as the chain carrier which is formed by electron transfer from the excited state of BNAH to benzyl bromide. However, the [Ru(bpy)3]2+-mediated photoreduction of benzyl bromide with BNAH occurs in the presence of [Ru(bpy)3]2+, where benzyl bromide is subject to two-electron reduction by [Ru(bpy)3]+which is formed by an electron transfer from BNAH to the excited state of [Ru(bpy)3]2+.
UR - http://www.scopus.com/inward/record.url?scp=37049099847&partnerID=8YFLogxK
U2 - 10.1039/P29840001705
DO - 10.1039/P29840001705
M3 - Article
AN - SCOPUS:37049099847
SN - 1470-1820
SP - 1705
EP - 1709
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 10
ER -