.sigma.-Naphthoquinodimethanes and .sigma.-phenanthroquinodimethanes. Isoindene-related species

William R. Dolbier, Jean Pierre Dulcere, Simon F. Sellers, Henryk Koroniak, Blane T. Shatkin, Thomas L. Clark

The Journal of Organic Chemistry · 1982 · 10.1021/jo00133a013

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★ 4.0 1 rating
5 : Major extension (new functional group) –
4 : Minor extension (no new functional group) ×1
3 : Reproduced as published –
2 : Reproduced with deviation –
1 : Did not work –
– : Extension failed / Inconclusive –

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Industry / CRO chemist
09 Aug 2026
★ 4 : Minor extension (no new functional group)

Only the bromination of primary alkyl alcohols was tested (PBr3 in DMF). The reaction proceeded well, although an excess of reagents is required; otherwise, the reaction tends to stall before reaching completion.