The Intramolecular Participation of Sulfide Linkage on the Reactivity of Carbenes and Diazoalkanes. II. Alkylcarbenes and Diazoalkanes Bearing Arylthio and Allylthio Groups on β-Carbon
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β-Arylthio- and β-allylthioalkylcarbenes were generated from the corresponding ketones by a modification of the Bamford-Stevens method. Chemical evidence for the formation of novel cyclic ylides, <I>i.e.</I>, thietanonium ylides, by an intramolecular electrophilic addition of the carbene to the sulfur atom was obtained. The resulting ylides underwent various types of rearrangements to afford cyclopropyl sulfides, thiaazulenes, thietanes, and/or tetrahydrothiophenes. The mechanisms and the relative amounts of the transition energies for these rearrangements are discussed. An intramolecular cycloaddition of β-allyl- and β-crotylthioalkyldiazoalkanes is also described. The final products of the reaction were 3-thiabicyclo[4.1.0]heptanes. A thiabicyclic pyrazoline, which is presumed to be an intermediate of the cycloaddition, could be isolated in the case of the thermal decomposition of 4-allylthio-4-methylpentan-2-one tosylhydrazone.
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