798 Bull. Chem. Soc. Jpn., 75, No. 4 (2002)
Decomposition of Arenediazonium Salts
three stock solutions would be diluted to give three or four differ-
ent solutions for analysis.
8
E. H. White, H. P. Tiwari, and M. J. Todd, J. Am. Chem.
Soc., 90, 4734 (1968).
Quantitative Photolytic Reactions. The following are repre-
sentative.
9
K. G. Rutherford, W. Redmond, and J. Rigamonti, J. Org.
Chem., 26, 5149 (1961); C. Sellers and H. Suschitsky, J. Chem.
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(i) 3-Fluorobenzenediazonium Tetrafluoroborate in TFE.
A solution of the arenediazonium salt (0.0185 g, 0.0882 mmol)
and undecane (0.022 g, 0.142 mmol) in TFE (3.0 mL) in a UV cell
was clamped to the outside of the photochemical reactor and irra-
diated. The reaction was monitored by UV, then, upon comple-
tion, was extracted between water and ether, and the ether phase
was analyzed.
(ii) 4-Methoxybenzenediazonium Tetrafluoroborate in Sat-
urated Aqueous Potassium Fluoride. A stirred solution of 4-
methoxybenzenediazonium tetrafluoroborate (730 mg) in saturat-
ed aqueous potassium fluoride solution (10.2 mol dm−3, 200 mL)
was photolyzed in the usual way and monitored by UV spectros-
copy. Upon completion (ca. 2 h), the products were extracted into
ether (4×50 mL); the combined extract was dried (MgSO4), fil-
tered, and evaporated under reduced pressure. GLC analysis
showed 4-methoxyphenol to be the only product.
10 K. Shinhama, S. Aki, T. Furuta, and J. Minamikawa, Synth.
Comm., 23, 1577 (1993).
11 E. A. Moelwyn-Hughes and P. Johnson, Trans. Faraday
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12 J. M. Insole and E. S. Lewis, J. Am. Chem. Soc., 85, 122
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We thank the EPSRC for studentships to KMcC, BS, and
PSJC, and Zeneca (formerly ICI) for financial support. We
also thank Drs J.H. Atherton and D. J. Moody for helpful dis-
cussions, and Mss H. Dowling and N. Martin for supportive
experimental work. HM thanks members of the Institute for
Fundamental Research in Organic Chemistry (IFOC) at
Kyushu University for hospitality during the writing of this
manuscript, and Professors S. Kobayashi and T. Sonoda for
many helpful discussions.
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