Eschenmoser fragmentation

The Eschenmoser fragmentation, first published in 1967, is the chemical reaction of α,β-epoxyketones (1) with aryl sulfonylhydrazines (2) to give alkynes (3) and carbonyl compounds (4).[1][2][3] The reaction is named after the Swiss chemist Albert Eschenmoser, who devised it in collaboration with an industrial research group of Günther Ohloff, and applied it to the production of muscone and related macrocyclic musks.[1][2][4] The reaction is also sometimes known as the Eschenmoser–Ohloff fragmentation or the Eschenmoser–Tanabe fragmentation as Masato Tanabe independently published an article on the reaction the same year.[5][6] The general formula of the fragmentation using p-toluenesulfonylhydrazide is:[3]

Several examples exist in the literature,[7][8] and the reaction is also carried out on industrial scale.

  1. ^ a b Cite error: The named reference Muscone1 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference Muscone2 was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference GenRxn was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Muscone3 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Tanabe1 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Tanabe2 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Example1 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Example2 was invoked but never defined (see the help page).