1-Indanone → Indene

Participants

Reaction Steps

Starting indanones J may be synthesized from commercially available 1-indanone F, shown by the following reaction sequence, by initial formation of the tosyl hydrazone (H2NNHTs, 1:1 eq./EtOH, 100° until solubilized) followed by methyllithium-induced elimination (3 eq./Et2O, 25°, 2.5 hours) to give indene G. Hydroboration-oxidation of G using standard conditions affords 1,2-oxygen transposition product H. Dess-Martin periodinane oxidation affords desired indanone J. Indanone J is converted in good yield to corresponding compounds of the invention as described hereinbefore. ##STR7##

Provenance & Evidence