173171-34-1Relevant academic research and scientific papers
Ring Expansion, Ring Contraction, and Annulation Reactions of Allylic Phosphonates under Oxidative Cleavage Conditions
Orr, Dupre,Yousefi, Nikolas,Minehan, Thomas G.
, p. 2839 - 2843 (2018)
Oxidative cleavage of cycloalkenylalkylphosphonates 1 followed by treatment with base gives rise to homologated cycloalkenones 2 in good to excellent yields. Subjecting cycloalk-2-enylphosphonates 3 to identical conditions provides the one-carbon ring-contracted compounds 4 in excellent yields. Oxidative cleavage of γ,δ-unsaturated ketophosphonates 6 followed by treatment with base affords 2-cyclopenten-1-ones 7 in good overall yields. This method may offer a practical alternative to existing methods for effecting one-carbon ring expansion, ring contraction, and annulation reactions.
Reaction of Phosphonate-Stabilized Carbanions with Cyclic Enones Bearing a β-Leaving Group
Mphahlele, Malose J.,Modro, Tomasz A.
, p. 8236 - 8240 (2007/10/03)
Reaction between α-lithiated alkylphosphonic esters and α,β-unsaturated cyclopentenones and cyclohexenones carrying a heteroatom substituent Y in the β-position was studied.Complete chemoselectivity was observed as a function of substituent Y.For Y = OMe exclusive addition-elimination at the β-carbon was observed, yielding α,β-unsaturated δ-ketophosphonates.The β-chloro-substituted substrates (Y = Cl) derived from cyclohexenone reacted exclusively at the carbonyl carbon, yielding (2-hydroxyalkyl)phosphonates with the retained chlorovinyl function.The alcohols, depending on the conditions, could be dehydrated to two different products.The reaction of 3-chlorocyclopent-2-en-1-one with diethyl (lithiomethyl)phosphonate occured at the β-carbon, but the ketophosphonate product was isolated in a stable enolic form.
