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(c) For related deacylating diazo transfer reactions of β-diketones with PNBSA, see: Taber, D. F.; Gleave, D. M.; Herr, R. J.; Moody, K.; Hennessy, M. J. J. Org. Chem. 1995, 60, 2283.
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85069282342
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note
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It is noteworthy that acyclic β-keto esters, contrary to our cyclic counterparts, normally undergo deacylating diazo transfer in preference to azidation and/or Favorskii-type rearrangement, irrespective of the aromatic or aliphatic ketone moiety and the sulfonyl azide reagent. This fact probably arises from comparatively easier production of monocyclic triazolines as well as from higher propensity of such monocyclic intermediates to suffer ring-cleavage fragmentations to diazo compounds.
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21
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Azide 21a had been previously reported, but no spectral data were available: Forster, M. O.; Müller, R. J. Chem. Soc. 1910, 97, 126.
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85069277503
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Commercially available (Lancaster)
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Commercially available (Lancaster).
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