Thermal rearrangement of some benzoin arylsulfonylhydrazone derivatives

Gaber, Abd El‐Aal M.; Mohamed, Omima S.; Aly, M. M.

doi:10.1016/j.jaap.2004.09.004

Cited by 5 publications

(1 citation statement)

References 24 publications

(21 reference statements)

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“…On the basis of the realization that methods forming the central C–C-bond are scarce, we wondered whether a protocol could be devised that, analogously to olefination reactions, would enable the formation of internal alkynes from two separate fragments. Our attention was drawn to the fragmentation of tosylhydrazones bearing an α-leaving group . Such reactions have the inherent advantage that no regioselectivity issues arise, which would, for example, be expected in the dehydration of ketones with two aliphatic substituents, but the respective protocols typically require harsh conditions and activated starting materials that have to be accessed over several synthetic steps.…”

Section: Introductionmentioning

confidence: 99%

The Direct Conversion of α-Hydroxyketones to Alkynes

et al. 2018

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Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C–C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.

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Section: Introductionmentioning

confidence: 99%