Journal of Organic Chemistry p. 3451 - 3456 (1980)
Update date:2022-08-04
Topics:
Lahousse, Hugo
Martens, Henri J.
Hoornaert, Georges J.
Treatment of 2,3-bis(bromomethyl)-6-methoxy-1-indenone (1) with various nucleophiles constitutes a one-step synthesis of 2,4-disubstituted 1-naphthalenols 3.The mechanism of this reaction has been explored.This study reveals the intermediacy of 3-(bromomethyl)-6-methoxy-2-methylene-1-indanones of type 7, which are thought to be formed by a SN2' substitution on the allylic bromide system of 1.A second nucleophilic attack on 7 leads to cyclopropinden-6-ones 9 via a homo SN2' substitution.The latter rearrange spontaneously into the 1-naphthalenols 3.With carefully controlled reaction conditions an intermediate of type 7 could be isolated; it has been used in separate experiments with other nucleophiles.Depending on the nucleophile, this leads either to naphthalenols 3 or to 8-oxoindeno<1,2-c>pyrrolidines 5.
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