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27644567840
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note
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The starting material ortho-iodobenzyl azide 1 was prepared by heating ortho-iodobenzyl bromide (1.5 g, 5 mmol) and sodium azide (400 mg, 6.2 mmol) at 100°C for 8 h in dry DMF (12 ml). After work-up and purification by chromatography on silica gel using 8% (v/v) ethyl acetate in hexane as eluent, the desired azide 1 was obtained in 82% yield.
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27644516091
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In a few cases, dimers were isolated and characterised unambiguously by spectroscopic and analytical data.
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50
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27644501144
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note
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2OTBS) was isolated by carrying out the reaction at room temperature. Various experiments were then carried with A under various reaction conditions. Among them, the desired cycloaddition occurred when A was heated in DMF at 115°C in the presence of triethylamine and a catalytic amount of cuprous iodide only. Without cuprous iodide starting material A was recovered.
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