𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Polyfunctionalized hexahydro-1 (2H)-pentalenones by rearrangement of bicyclic 1,2-oxazine N-oxide derivatives

✍ Scribed by G. Barbarella; S. Brückner; G. Pitacco; E. Valentin

Book ID
104203056
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
666 KB
Volume
40
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

The title heterocycles rearrange into a mixture of diastereoisomeric hexahydro-l(ZH)-pentalenone derivatives, which undergo nucleophilic eliminative ring fission by methanol to give I-amino-2-nitroalkylated cyclopentancarboxylic esters. The X-ray structure determination of hexahydro-2-methyl-2-nitro-3-phenyl-6a-(I-piperidinyl)-1(2H)-pentalenone IZS-(2a,3a,3aa,6aa)l is also reported. Cyclic enamines have been shown 112 to react with nitroolefins to give 1,2-oxazine N-oxide derivatives, whose stabilities are related to the nature of the substituents R' and R2 on the heterocyclic ring. Usually they open into the corresponding nitroalkylated enamines.

📜 SIMILAR VOLUMES

ChemInform Abstract: Unexpected Spontane
ChemInform Abstract: Unexpected Spontaneous Ring-Contraction Rearrangement of Trifluoromethylated 1,2-Oxazine N-Oxides to 1-Pyrroline N-Oxides.
✍ Vladislav Yu. Korotaev; Alexey Yu. Barkov; Pavel A. Slepukhin; Mikhail I. Kodess 📂 Article 📅 2012 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

## Abstract Reactions of cyclohexanone‐derived enamines (I) with nitrobutene (II) affords cyclic nitronates (III) instead of the expected isomeric nitrones of type (V).