Diallyl adipate

These discussions have been extended to the bulk polymerizations of diallyl adipate (DAA), diethylene glycol bis (allyl carbonate) (DEGBAC), and diallyl diphenate (DAD) accompanied by a greatly delayed gelation The monomer type, actual gel point (%), theoretical gel point (%) are, respectively, as follows DAA, 25.6, 3.6 DEGBAC, 23.0, 3.7 DAD, 29.2, 3.4. 

A rapid copolymerization of diallyl adipate with an unsaturated polyester using a small quantity of lauryl mercaptan and stannous chloride along with dibenzoyl peroxide has been described. This patented procedure is of particular interest in the manufacture of flexible coatings or textiles. Procedure 9-2 may be investigated as a general method of accelerating conventional peroxide-initiated polymerizations provided the patent does not impose restrictions on such work. 

A mixture of 65 gm of an unsaturated polyester, 35 gm of diallyl adipate, 2 gm of recrystallized dibenzoyl peroxide, and 0.4 ml of laiuyl mercaptan (CAUTION stench), and 0.7 ml of a saturated solution of stannous chloride in DMF is prepared at room temperature. 

Allyl radicals are also obtained by irradiation of allylvinyl acetate, diallyl adipate, diallyl sebacate, triallyl phosphate, and triallyl cyanurate. 

The synthesis of a series of a-aryl-P-keto allyl esters was accomplished by first preparing cyclopentanone- and cyclohexanone-derived P-keto allyl esters 3 and 4 (Scheme 6.1). This was achieved via Dieckmann condensation of commercially available diallyl adipate using NaH as the base to generate cyclopentanone P-keto allyl ester 3 in 73 % yield. Similarly, diallyl pimelate, prepared by transesterification... 

Allyl /3-keto carboxylates and allyl enol carbonates undergo a palladium-catalyzed decarboxylation-dehydrogenation to yield o, S-unsaturated ketones in usually high chemical yield and with good selectivity. Following this approach, it was possible to obtain 2-methyl-2-cyclopentenone in two steps from diallyl adipate in a procedure that could be convenient for large-scale preparations (eq 62). ... 

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