Bornyl chloroformate

More recently, Oohara and Imamoto used bornyl chloroformate to resolve racemic tcrt-butylmethylphosphine borane (rac-100), as depicted in Scheme 2.35. 

Benzyl benzoate Bornyl acetate 2-Butanol n-Butyl acetate t-Butyl alcohol Butylene glycol dicaprylate/dicaprate Butyrolactone Caprylic/capric/lauric triglyceride Caprylic/capric/linoleic triglyceride Caprylic/capric triglyceride Caprylic/capric triglyceride PEG-4 esters Carbon tetrachloride Chlorobenzene Chloroform Coconut (Cocos nucifera) oil... 

To a small, heavy-walled polymerization tube with a connection to a vacuum system are added 1.0 gm (0.005 mole) of 5-hydroxy-4-hydroxy-methylpentanol diethylacetal (n 1.4530-1.4532) along with a small crystal of /7-toluenesulfonic acid monohydrate. The tube is heated to 120°C under a reduced pressure (0.02 mm Hg) for 15-30 min. The reaction mixture is cooled, neutralized with concentrated ammonium sulfate, and extracted with chloroform. The chloroform extract is decolorized with Darco and evaporated to dryness under reduced pressure to give the polymer [average mol. wt. (from bornyl bromide) 1190 100 IR 3440 cm (OH) and 1736 cm (>C—O) softening point 49°C]. 

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