The haloindenes are important synthetic precursors. We used haloindenes as precursors for the generation of various indenyl radicals (from 1-indenyl to 7-indenyl) which react with unsaturated hydrocarbons, such as acetylene and vinylacetylene, with formation of an additional aromatic ring, to study the growth mechanisms of polycyclic aromatic hydrocarbons (PAH). Methods for the synthesis of most reactive of iodoindens are limited, although they could serve as convenient substrates for cross-coupling reactions. Reported synthesis of iodoindenes employs expensive nitroindanone as substrate and requires several steps which include separation of unstable aminoindene intermediate providing 5-iodoindene or 6-iodoindene in 20% and 7% respectively. We report straightforward synthesis of 5, 6, and 7-iodoinenes isomers from readily available 5, 6, and 7-aminoindanones which also employs simple ubiquitous reagents. Thus, diazotization-Sandmeyer reaction of 5, 6, and 7-aminoindanones A with t-BuONO/CH2I2/I2/CuI in THF at 60 oC for 30 min afforded corresponding iodoindanone B (&gt;90%). Reduction with NaBH4 provided secondary alcohols C (&gt;95%) and subsequent dehydration with aqueous HCl under reflux yielded selectively corresponding 5, 6, and 7-iodoinenes D (&gt;70%). Isomerization of indenes was not observed during this reaction sequence. Application of iodoindenes for the synthesis of the corresponding enyne derivatives will be also discussed.

Novel synthesis of 5-, 6-, or 7-iodoindenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.