Heptenes hydration

C10H17N7O4 saxito)dn hydrate 35523-89-8 356.15 30.254 1.2 20694 C10H18O 4-ethyl-6-methyl-5-hepten-2-one 104035-66-7 480.98 42.060 2... 

The Diels-Alder reaction was utilized to construct bicyclo [2.2 1]heptane or bicyclo[2 2 l]heptene structures The reaction of isopropylidenecyclopentadiene with maleic anhydride produced the endo and exo configurational isomers of 8-isopropylidenebicyclo[2.2.1] hept-2-ene-5,6-dicarboxylic anhydride Similar reactions were applied to unsubstituted and l-(methoxycarbonyl)cyclopentadienes to give the corresponding anhydrides The anhydrides were reduced to alcohols, which were then allowed to react with thionyl chloride or tosyl chloride to give cyclic sulfites or tosylates Reaction of the tosylates with lithium chloride gave chlorinated compounds Hydration of the double bonds of the chlorinated compounds was accomplished by hydroboration-oxidation Diol 31 thus obtained was converted to 5,6-bis(chloromethyl)-7-isopropylidene-bicyclo[2 2 1] heptan-2-one [33] by chromium trioxide oxidation of the secondary hydroxyl group followed by dehydration at the C-7 substituent. 

The hydration of olefins to alcohols has been carried out on a large scale by hydrolyzing the sulfuric acid esters formed by the absorption of the olefins in sulfuric acid. In the case of the higher olefins these reactions occur with comparative ease. Thus, isobutylene may be hydrated to tertiary butanol in cold, moderately concentrated sulfuric acid.81 Some of the pentenes and heptenes may be hydrated in dilute (5 to 10 per cent) solutions of formic, acetic, or oxalic acids as well as in weak solutions of the mineral acids.83 With 60 per cent concentrations of hydroiodic acid, isobutylene yields the iodide almost exclusively, but at lower concentrations increasing amounts of the alcohol are fonned84 Similar phenomena attend the absorption of the higher olefins in hydrobromic acid. Hydrochloric acid, on the other hand, does not show such marked activity toward the higher olefins ind is practically devoid of activity toward ethylene. 

Acid-Catalyzed Hydration of 2-Methylpropene 227 Hydroboration of 1-Methylcyclopentene 233 Oxidation of an Organoborane 235 Bromine Addition to Cyclopentene 237 Epoxidation of Bicyclo[2.2.1]-2-heptene 240 Free-Radical Addition of Hydrogen Bromide to 1-Butene 243... 

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