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17.4.5.2.1.5.2.2 Variation 2: Pyrolysis of 2-Haloindan-1-yl Azidoformates

DOI: 10.1055/sos-SD-017-01150

Surman, M. D.; Hutchings, R. H.Science of Synthesis, (200417790.

Spray-vacuum pyrolysis (SVP) of trans-2-bromoindan-1-yl azidoformate (201) gives cyclopent[b]azepine (5) in good yield (Scheme 58).[‌137‌,‌138‌] The product is formed irrespective of the relative stereochemistry of the halo and azidoformate moieties, and either chloro or bromo substitution affords the desired product. The 4-bromo and 3-methoxy derivatives can also be formed in a similar fashion, albeit in diminished yields (30% and 50%, respectively). Cyclopent[b]azepine (5) is unstable in daylight, or in the presence of oxygen, but can be stored as a solution in the dark under nitrogen.

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