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[1,4] migratioms in acid catalyzed rearrangements of β-naphthalenones

✍ Scribed by Bernard Miller; Mohammed Reza Saidi

Book ID
104213645
Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
206 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

Received in USA 25 Jamaxy 1975; xeoelved in UK for publioatlon 17 Maroh 1975) Reaction of naphthalenone Lwith protic acids (such as sulfuric acid In acetic acid or water) gives approximately equal yields of the [3,41 rearrangesent product 2 and the [1,5] rearrangement product &2

These products can both be rorsed by syxmetry allowed suprafacial sigsatropic shifts.3

We have now observed that when &is reacted with a 0.2 M solution of sulfuric acid in acetic auhydride for two hours, it gives products corresponding to neither gnor 3_ Instead, the rearrangement product 4 is obtained in 60% yield, accaapauied by the cleavage product lmethyl-P-naphthyl acetate. =.

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Novel acid catalyzed migrations in β-nap
Novel acid catalyzed migrations in β-naphthalenones
✍ Bernard Miller; Mohammed R. Saidi 📂 Article 📅 1972 🏛 Elsevier Science 🌐 French ⚖ 206 KB

The normal dienoue-phenol rearrangements of linearly-conjugated cyclohexadienones (e.g., &+2) are prevented in the a-naphthalenone I.\* Instead, a methyl group in 1 migrates to the carbonyl carbon to give carbonium ion 4, which then gives rise to the naph-thy1 acetate 2. No further migration of a me

A [3,4] Allyl Shift in a thermal rearran
A [3,4] Allyl Shift in a thermal rearrangement of a β-naphthalenone1
✍ Bernard Miller; Welh-Oh Lin 📂 Article 📅 1978 🏛 Elsevier Science 🌐 French ⚖ 119 KB

PQrations of ally1 p~ouos in acid catalyzed rearran~ments of cyclohexadienones give products resulting from [1,2], [1,3], [1,4], [1,5], [3,3], and [3,4] shifts.2 In contrast, only Cope and Claisen ([3,3]) mivations of ally1 \_g~ups have been observed in thermal rearrangements