A brief,
efficient method has been developed for the removal of
the allyl protecting group from allyl carboxylic esters using a Co(II)/TBHP/(Me2SiH)2O catalytic system. This facile strategy displays
excellent chemoselectivity, functional group tolerance, and high yields.
This transformation probably occurs through the hydrogen atom transfer
process, and a Co(III)–six-membered cyclic intermediate is
recommended.
1,3,5-%oxane (1) and 1,3-dioxep-5-ene (2) were copolymerized with BF30Et, at 65°C. The products, after base hydrolysis, were characterized by 13C and 'H NMR and were found to assume the chemical structure 4 of a copolymer containing oxymethylene and oxy-2-butenylene units with 4-hydroxy-2-butenyl and methoxy end groups, with the ratio of hydroxy-2-butenylene to methoxy end groups varying with experimental conditions. The copolymer demonstrates crystallinity and thermal stability comparable to poly(trioxane-co-ethylene oxide)s. Copolymer melting point was observed to decrease with increasing comonomer incorporation. The upper limit for incorporation of the comonomer 2 was found to be ca. 4 mol per cent. Viscosity and end group analysis (by 'H NMR) indicate molecular weights in the range of lo4 to lo5. The comonomeric unit demonstrates the ability to act as both a stopper against unzipping and as a trap for certain degrading agents.
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