144363-60-0Relevant articles and documents
Reaction of 2,6-Disubstituted Phenols with Vinyllead Triacetates and Alk-1-ynyllead Triacetates: Synthesis of 6-Vinyl- and 6-Alkynyl-Cyclohexa-2,4-dienones and Crystal Structure of 1,3,5,7-Tetramethyl-3,5-bis(phenylethynyl)-1,3,4,4a,5,8a-hexahydro-1,4-ethenonaphthalene-2,6-dione
Hambley, Trevor W.,Holmes, Rodney J.,Parkinson, Christopher J.,Pinhey, John T.
, p. 1917 - 1922 (2007/10/02)
(E)-Styryllead triacetate 9, generated by reaction of lead tetraacetate with trimethylstannane 7, has been found to react with 2,4,6-trimethylphenol 1 to give the 6-(E)-styrylcyclohexa-2,4-dienone 11 in high yield.This electrophilic vinylation reaction has been investigated for the vinyllead triacetates 9 and 10 and the 2,6-dimethylphenols 1, 13, 14 and 15.An analogous alkynylation reaction occurred when phenylethynyllead triacetate 24 was treated with 2,4,6-trimethylphenol; however, the product in this case, cyclohexadienone 25, underwent a Diels-Alder dimerisation to give the 1,4-ethenonaphthalene 26.The product 28 from a reaction of the phenylacetylenelead compound 24 and 2,6-dimethylphenol behaved similarly, and here the 1,4-ethenonaphthalene structure 27 for the dimer was determined by single crystal X-ray analysis.
