Abstract
3,4,5,6-Tetra- O-acetyl- d- lyxo-hexosulose 1-acetylphenylhydrazone 2-phenylhydrazone ( 10) was transformed into 5-( d- glycero-1,2-diacetoxyethyl)-3-formyl-1-phenylpyrazole acetylphenylhydrazone ( d- 4, n = 3) in boiling acetic anhydride containing anhydrous sodium acetate. Racemic 3,4,6-tri- O-acetyl-5-deoxyhex-4-enos-2-ulose 1-acetylphenylhydrazone 2-phenylhydrazone ( 11) was isolated as an intermediate in the reaction performed in the absence of sodium acetate. The cyclisation of 11, via allylic rearrangement, into dl- 4 ( n = 3) and 5-( dl- glycero-1,2-dihydroxyethyl)-3-formyl-1-phenylpyrazole acetylphenylhydrazone ( dl- 3, n = 3) in acidic, neutral, and basic media is described.
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