Journal of the Chemical Society - Faraday Transactions p. 311 - 319 (1990)
Update date:2022-08-23
Topics:
Haenel, Matthias W.
Richter, Udo-Burckhard
Solar, Sonja
Getoff, Nikola
1,2-Di(1-naphthyl)ethane (1,2-DNE) has been used to study the radiation-induced C-C bond cleavage of the ethane linkage.Pulse radiolysis was applied both in the absence and presence of NaAlH4 and NaAlH2(OR)2 used as scavengers for solvent cations.In the presence of the sodium aluminium hydrides the radical anions of 1,2-DNE are stabilized by the metal cation, resulting in the formation of radical anion/sodium cation pairs (Na+, 1,2-DNE.-), these species have a rather long lifetime (τ>2 ms) in DME as well as in THF, and show three absorption bands at 330, 370 and 750 nm.In THF ε370=14000 dm3 mol-1 cm-1 and ε750=5000 dm3 mol-1 cm-1 were established.Cleavage of the ethano bridge of 1,2-DNE was achieved by means of steady-state as well as multi-pulse radiolysis in the presence of alkali-metal aluminium hydrides.The efficiency of this process was studied by using NaAlH4, NaAlH2(OR)2, NaAlH2Et2, NaAlEt4 and LiAlH4 in THF as well as in DME.The most efficient C-C bond cleavage results from the successive attack of two sodium cation/electron ion pairs (Na+, e-) forming the unstable dianions (2 Na+, 1,2-DNE2-).These decompose under scission of the ethano bridge, producing naphthylmethyl carbanionic fragments C10H7CH2-Na+ which supposedly form aluminate salts, e.g.C10H7CH2AlH3-Na+, with AlH3 generated in the scavenging processes.From these aluminate salts 1-methylnaphthalene is obtained through hydrolysis.
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