title: Oxetan-3-ones from allenes via spirodiepoxides.
abstract: Two concise methods for generating oxetan-3-ones from allenes are reported. The first method employs allene epoxidation, opening of the spirodiepoxide by a halide nucleophile, and then intramolecular displacement of a halide by an alkoxide. The second method involves allene epoxidation and then thermal rearrangement of the corresponding spirodiepoxide to oxetan-3-one. The two methods are complementary and stereochemically divergent. Computational analysis of the thermal rearrangement is also described.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
authors.forename: Rojita
authors.initials: R
authors.lastname: Sharma
authors.forename: Lawrence J
authors.initials: LJ
authors.lastname: Williams
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D004988:Ethers, Cyclic; D013141:Spiro Compounds; C025947:propadiene; C005287:oxetane