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- W2949166688 abstract "The reactions of several thioketones containing a conjugated CC bond with diazo compounds were investigated. All of the selected compounds reacted via a 1,3-dipolar cycloaddition with the CS group and subsequent N2 elimination to yield thiocarbonyl ylides as intermediates, which underwent a 1,3-dipolar electrocyclization to give the corresponding thiirane 25, or, by a subsequent desulfurization, to give the olefins 33a and 33b. None of the intermediate thiocarbonyl ylides reacted via 1,5-dipolar electrocyclization. If the α,β-unsaturated thiocarbonyl compound bears an amino group in the β-position, the reactions with diazo compounds led to the 2,5-dihydrothiophenes 40a–40d. In these cases, the proposed mechanism of the reactions led once more to the thiocarbonyl ylides 36 and thiiranes 38, respectively. The thiiranes reacted via an SNi′-like mechanism to give the corresponding thiolate/ammonium zwitterion 39, which underwent a ring closure to yield the 2,5-dihydrothiophenes 40. Also in these cases, no 1,5-dipolar electrocyclization could be observed. The structures of several key products were established by X-ray crystallography." @default.
- W2949166688 created "2019-06-27" @default.
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- W2949166688 date "2006-12-01" @default.
- W2949166688 modified "2023-10-18" @default.
- W2949166688 title "Reactions of Thioketones Possessing a Conjugated CC Bond with Diazo Compounds" @default.
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- W2949166688 doi "https://doi.org/10.1002/hlca.200690274" @default.
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