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hexanone was slowly added and the resulting mixture was stirred for 24 hr at 0°. Then water was added (10-15 ml) slowly to decompose the excess hydride and to hydrolyze the reaction mixture. The boronic acid formed was oxidized by adding 66 ml of 3 N sodium hydroxide followed by dropwise addition of 66 ml of 30% hydrogen peroxide (vigorous reaction). The resulting mixture was stirred at 30-50°for 1 hr. Then the reaction mixture was extracted five times with 60-ml portions of ether and the ether extract was washed five times with equal amounts of ice water to remove diglyme. The ether extract was dried over magnesium sulfate. After the solvent was removed, the mixture was distilled at 20 mm to remove cyclohexanol (from the oxidation). The pressure was then reduced to obtain 27 g (99%) of 2-cyclohexylcyclohexanol (cis 96% by glpc analysis on a TCEP column), bp 117-118°( 6 mm), mp 59-61°, p-nitrobenzoate mp 112-114°(lit.21 mp 61°, p-nitrobenzoate mp 113°).B. Preparation of czs-2-Phenylcyclopentanol. To a solution of 150 ml (150 mmol) of a 1.0 M solution of disiamylborane in THF in a 500-ml flask maintained at 0°under nitrogen was added 14.4 g (90 mmol) of 2-phenylcyclopentanone over a period of 15 min. The resulting mixture was stirred at 0°for 24 hr and then worked up as usual. The volatile solvents and siamyl alcohol were removed at 40-45°(10 mm). Distillation of the residue yielded 11 g (75%) of 2-phenylcyclopentanol (cis 97% by glpc), bp 118°( 8 mm), n20o 1.5433, p-toluenesulfonate mp 96-97°[ lit.22 pure cis isomer, bp 111-113°(5 mm), n20d 1.5460, p-toluenesulfonate mp 97-98°].

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Seven new compounds derived from exo-adducts of fulvenes and maleic anhydride have been prepared. An analysis of the infrared spectra of these compounds determined in Nujol mull and in carbon tetrachloride solution has shown that lactones V-XI are correctly represented as six-membered (S-)lactones. It has also been shown that these lactones are readily susceptible to hydrogen bonding and that care must be exercised in assigning a ring size on the basis of spectral data where intermolecular associations may give rise to frequencies not characteristic of the free lactonic carbonyl stretching.

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