𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Novel acid catalyzed migrations in β-naphthalenones

✍ Scribed by Bernard Miller; Mohammed R. Saidi

Book ID
104245404
Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
206 KB
Volume
13
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

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 methyl group to give 6 occurs, since formation of 5 would require disruption of the aromaticity of the second ring.

Cif, CIr, 03 3 / 0 We have now investigated the migrations of ally1 groups in &mphthalenoues.

In

📜 SIMILAR VOLUMES

[1,4] migratioms in acid catalyzed rearr
[1,4] migratioms in acid catalyzed rearrangements of β-naphthalenones
✍ Bernard Miller; Mohammed Reza Saidi 📂 Article 📅 1975 🏛 Elsevier Science 🌐 French ⚖ 206 KB

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