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608 R 75 With aldehydes, a-halogenated sulfides give thioether ~ x i r a n e s . ~ ”a-mercaptocarbonyl compounds react with chloracrylonitrile to yield dihydrothiophene oxirane derivatives; under phase-transfer conditions the leaving group is incorporated intramolecularly (Eq. 610 With ketones, a-chlorosulfoxide forms a-epoxysulfoxides (Eq. 612 A modified variant of the Darzen’s reaction has been described for the production of new derivatives by conjugate addition of nucleophiles to haloolefins (Eqs.
535Exclusively cis product was obtained from a highly substituted octalin with NazCr04, KMn04, or ozone (Eq. lg9 Hypochlorous acid and its salts may be utilized for the epoxidation of electronpoor olefins. ’~~ Presumably rotation occurs before the ring-closure of the carbanion formed in the attack by the OCI- anion. 538 The osmium tetroxide-catalyzed epoxidation of olefins with sodium chlorate has been reported. It was proved that the epoxy-oxygen originates Oxiranes 40 exclusively from the chlorate.
The trans-oxirane is formed from meso-65 and the spiro compound (phosphorane) from dl-65 (Eq. 550,551 Ph-CH-CH- I I OH OH 65 -Ph (54) Oxiranes 42 Quantitative yields of oxiranes can be obtained from vicinal diols by the joint application of triphenylphosphine and DEAD (Eq. ”~ By the action of heat. 554~555 Disecondary or ditertiary 1,2-diols react with diaryldialkoxysulfurane 66 by antiperiplanar intramolecular nucloephilic displacement via a 0-hydroxyalkoxysulfonium ion intermediate 67 (Eq. 556 OC(CF,),Ph 66 L 67 From the corresponding diols, cis- and trans-divinyloxiranes can be prepare2 by elimination of the monotosylate obtained via the disodium a l ~ o h o l a t e .