Allyl alcohol reaction with carbon tetrachloride

A third approach to the preparation of allyl lluorovinyl ethers is the reaction of an allylic alcohol with trifluoroacetaldehyde, as illustrated by an alternative synthesis of 37a.17 Cinnamyl alcohol (47) forms with trifluoroacetaldehyde a hemiacetal, which is converted into bromide 48 via the mesy late. Reductive elimination affords 37a, which undergoes Claisen rearrangement within one hour in refluxing carbon tetrachloride to give 2,2-difluoro-3-phenylpent-4-enal (38a).17... 

Mol. wt. 285.95, m.p. 195°, dec. Suppliers Arapahoe, A, B, MCB. A useful reagent comparable to N-bromosuccinimide, it effects allylic bromination, dehydrogenation, substitution of active hydrogen, and oxidation of secondary alcohols. Review. Attempted side-chain bromination of 2,4-dibenzoylamino-6-methylquinazoline with bromine in chloroform led instead to elimination of the 4-benzoyl group, and reaction with N-bromosuccinimide in chloroform or carbon tetrachloride was... 

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