Allyl acetate, ozone reactions with

In the late fifties Regie Nationale des Usines Renault (86) described the preparation of allyl ethers through reaction of alkali cellulose with allyl halides in carbon tetrachloride or benzene. With products having degrees of substitution between 0.2 to 0.8 graft copolymerization could be achieved when activated by pretreatment with air or ozone or by initiation with peroxide catalysts with styrene, acrylonitrile, vinyl acetate, or acrylates. 

The rate constants for oxidation of a series of cycloalkenes with ozone have been determined using a relative rate method. The effect of methyl substitution on the oxidation of cycloalkenes and formation of secondary organic aerosols has been analysed.155 Butadiene, styrene, cyclohexene, allyl acetate, methyl methacrylate, and allyl alcohol were epoxidized in a gas-phase reaction with ozone in the absence of a catalyst. With the exception of allyl alcohol, the yield of the corresponding epoxide ranged from 88 to 97%.156 Kinetic control of distereoselection in ozonolytic lactonization has been (g) reported in the reaction of prochiral alkenes.157... 

Lee S-H, Mendenhall GD (1988) Relative yields of excited ketones from self-reactions of alkoxyl and alkylperoxyl radical pairs. J Am Chem Soc 110 4318-4323 Leitzke A, Reisz E, Flyunt R, von Sonntag C (2001) The reaction of ozone with cinnamic acids - formation and decay of 2-hydroperoxy-2-hydroxy-acetic acid. J Chem Soc Perkin Trans 2 793-797 Lodhi ZH, Walker RW (1991) Oxidation of allyl radicals kinetic parameters for the reactions of allyl radicals with H02 and 02 between 400 and 480 °C. J Chem Soc Faraday Trans 87 2361-2365 Martini M, Termini J (1997) Peroxy radical oxidation of thymidine. Chem Res Toxicol 10 234-241... 

Reaction of allylic alcohol 396 with paraformaldehyde using a catalytic amount of p-toluenesulfonic acid gave cyclic carbamate 397, which upon reduction with lithium aluminum hydride afforded aminodiol 398. Oxidative cleavage of the double bond of 398, achieved by dry silica gel ozonization (80JA5968) of the trifluoro acetate salt of aminodiol 398, gave ( )-5-epi-desosamine (399) (Scheme 49). 

ALLYL PHENYL ETHER (1746-13-0) C ipO Combustible liquid (flash point 143°F/62°C). May form peroxides on contact with air. Violent reaction may occur with strong oxidizers, strong acids acetyl peroxide boron trifluoride aluminum hydride (possible explosion). Incompatible with nitrosyl perchlorate, ozone (may form explosive ethyl peroxide, aldehyde and acetic acid). On small fires, use dry chemical powder (such as Purple-K-Powder), foam, or CO2 extinguishers. 

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