| Title: |
Cyclopropyl building blocks in organic synthesis. Part 81: Striving for unusually strained oxiranes: epoxidation of spirocyclopropanated methylenecyclopropanes |
| Authors: |
Frank, D.; Kozhushkov, Sergei I.; Labahn, T.; de Meijere, Armin |
| Contributors: |
Frank, D.; Kozhushkov, Sergei I.; Labahn, T.; de Meijere, Armin |
| Publisher Information: |
Pergamon-elsevier Science Ltd |
| Publication Year: |
2002 |
| Collection: |
Georg-August-Universität Göttingen: GoeScholar |
| Description: |
1-Oxa[3]triangulane 13, the epoxide of methylenespiropentane, is thermally stable up to 300degreesC, but immediately rearranges to spiro[2.3]hexan-4-one (7) in the presence of lithium iodide at ambient temperature. The permethylated bicyclopropylidene 10 is simply less reactive than the parent bicyclopropylidene (6a) towards dimethyldioxirane, but yields the isolable epoxide 11 (94%) with mCPBA. In contrast, the partially or fully spirocyclopropanated bicyclopropylidenes 18, 20, and 22, upon treatment with mCPBA or dimethyldioxirane, did not furnish the corresponding epoxides, but underwent oxidation with rearrangement to the corresponding cyclobutanones 19, 21 and 23 in yields of 59, 100 and 97%, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved. |
| Document Type: |
article in journal/newspaper |
| Language: |
unknown |
| Relation: |
000177692300003 |
| DOI: |
10.1016/S0040-4020(02)00695-6 |
| Availability: |
https://resolver.sub.uni-goettingen.de/purl?gro-2/39770; https://doi.org/10.1016/S0040-4020(02)00695-6 |
| Rights: |
info:eu-repo/semantics/openAccess |
| Accession Number: |
edsbas.4E2D4048 |
| Database: |
BASE |