Synthesis of ethyl ?-(2,2 -dimethyltetrahydro-4-pyranyl)-?-oxopropionate

Vartanyan, R. S.; Kazaryan, Zh. V.; Vartanyan, S. A.

doi:10.1007/bf00474084

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2016

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“…14,15 There is a single previous example of this approach in which a tetrahydropyran-containing ylide 1 was prepared and subjected to conventional pyrolysis at 200-250°C (heating the solid above its mp) to afford alkyne 2 in 75% yield (Scheme 2). 16 …”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles

et al. 2016

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A range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2-dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure determination of each type. The X-ray structures confirm the PvC and CvO functions to be syn and all the compounds undergo thermal extrusion of Ph 3 PO to give the corresponding alkynes. In some cases there is also competing loss of Ph 3 P to give different carbene-derived products and evidence has been obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.

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Section: Introductionmentioning

confidence: 99%