Welcome to LookChem.com Sign In|Join Free

Article Doi

Some Rearrangements of Unsaturated Phosphonate Esters

DOI: 10.1039/P19810002127

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2127 - 2133 (1981)

Update date:2022-08-05

Topics:

Authors:

Cooper, DianneCooper, Dianne

Trippett, StuartTrippett, Stuart

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19810002127

α-Hydroxyalk-2-enylphosphonates undergo Claisen orthoester rearrangement on heating with orthoesters, and their arylsulphenates undergo <2,3>-sigmatropic rearrangement to give 3-arylsulphinylalk-1-enylphosphonates.The addition of allyloxide anion to the central carbon of the allene Me2C=C=CHP(O)(OEt)2 is followed by rapid Claisen rearrangement of the resulting allylic carbanion to give the two possible β-ketoalkylphosphonates.Allenic phosphonates of the general formula R1R2C=CHnCR3=C=CHP(O)(OEt)2 have been prepared: when R1 = R2 = H, R3 = Me, and n = 2, Cope rearrangement occurs to give isomeric dienes; when R1,R2,R3 = Me and n = 0, <1,5> hydride shift gives a triene which then cyclises to a cyclohexadiene; when R1 = Me, R2 = H, R3 = H or Me, and n = 0, the diene component can be used in Diels-Alder reactions.

View More

Products guided by the article

Product name:diethyl 3,5-dimethylcyclohexa-2,4-dienylphosphonate

Cas No:79238-60-1

79238-60-1

R&D Labs maybe for 79238-60-1

Relevant to this article

Hot Product