Generation and transformation of the [3.3.1]propellane skeleton by thermal rearrangements

Krämer, Guido; Kolshorn, Heinz; Meier, Herbert

doi:10.1016/s0040-4039(00)74405-4

Cited by 4 publications

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“…A cyclooctyne system can also be generated from a corresponding 1,2,3-selenadiazole, which is easily prepared by converting cyclooctanone to its semicarbazone, followed by its subsequent reaction with selenium dioxide. [14][15][16] However, the transformation of cycloocta-1,2,3-selenadiazole derivatives into cyclooctynes requires harsh conditions, such as thermolysis at temperatures over 115 1C, [17][18][19] thermolysis on copper powder, [20][21][22][23][24] or a reaction mediated by n-BuLi. 14 Such conditions limit the direct use of cycloocta-1,2,3-selenadiazoles for the labeling of biomolecules and the isolation of a generated cyclooctyne system must precede the azide-cyclooctyne conjugation.…”

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confidence: 99%

Study and application of noncatalyzed photoinduced conjugation of azides and cycloocta-1,2,3-selenadiazoles

et al. 2016

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The non-catalyzed cycloaddition of eight structurally different azides with cyclooctyne generated in situ by the photolysis of cycloocta-1,2,3-selenadiazole gives 1,2,3-triazole derivatives as the main products. The application of this reaction was demonstrated by the photoconjugation reaction of cycloocta-1,2,3-selenadiazole with an avidin-modified biotin complex to introduce a new strategy in the non-catalyzed synthesis of bioconjugates.

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