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4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted...
An application of the perturbation theory to the [4+2] addition of butadiene has demonstrated that the effect of secondary orbital interactions should be much less significant than has been assumed within the frontier orbital scheme. This has been confirmed by a numerical analysis with respect to the endo transition state of the Diels-Alder reaction between butadiene and maleic anhydride.
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