We wish to report the first example of a zinc-catalyzed rearrangement of the bicycle [P.l.O]pentane ring system. Namely, the rearrangement of I-Phenylbicyclo[2.1.O]pentane(b) with a catalytic amount of zinc iodide in benzene (2 hr, 60') to give as the sole product 3-phenylcyclopentene(2a).
Synthesis of 1-oxaspiro[2.2]pentanes. Rearrangement to cyclobutanones
โ Scribed by Donald H. Aue; Michael J. Meshisnek; Dale F. Shellhamer
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 272 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Oxaspiro[2.2]pentanes have recently been reported; 394 the synthesis and reactivity of this new heterocyclic system promises to be of considerable synthetic and mechanistic interest. We have found per-acid oxidation of methylenecyclopropanes provides a convenient synthesis of several l-oxaspiro[2.2]pentanes. We report here on the forumtion of some oxaspiropentanes, their thermal reactivity, and their conversion to cyclobutanones with Lewis acids.
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