l-Acetyl-l-methylcyclohexane: bp 68-70°(7 mm) [lit.26 bp 80-8.5°(16 mm)]; 13.8 g (66% based upon 150 mmol of olefin) isolated; ir 1700 cm-1; nmr r 8.0 and 9.0 [sharp s, H3CCOCCH8]; vpc (130°a nd 150°) 18 showed a single compound. The 2,4-DNP had a melting point of 131-132°( lit.26 mp 132°) and the semicarbazone melted at 183-185°(lit.26 mp 186-187°).3,3-Dimethyl[3.2.1]bicyclooctanone-2 (7): bp 30-40°(0.3 mm); ir 1710, 3050, and 1610 cm-1 (the latter indicated olefinic contamination); vpc (200°)18 indicated three compounds present. The distillate, dissolved in petroleum ether (bp 30-60°), was placed upon a column containing 30 g of neutral alumina. Elution with petroleum ether yielded an unidentified olefin, ir 3050 and 1610 cm-1, no carbonyl or hydroxyl absorptions present.Elution with 50% (v/v) benzene-petroleum ether yielded 2 g of 7 (25) O.
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