['nicotine', 'N-ox1de', "with'methylmagne51um", 'bromlde', 'furnishes', 'both', '2-,;a*‘”', '-""{f,‘,‘,', '.', 's', 'vthe', 'effects', '".:', "~'of", 'solvent', '‘4.‘_', '‘L', 'v.', '-_’', '‘.:“', ';«—.’1', '.', "?_.'\\,", '."\\;;»,,‘-4“', ';', '.', '\\9.', 'temperature', "'and", 'relatlve', 'reagent', 'concentration', 'are', '-t', 'presented', 'and', 'discussed', 'The', 'radical', 'methylations', 'lead', 'to', '2-', ':h4-;', 'and', '6—methy1n1cotines', 'and', '4', '6', 'dlmethylnlcotine', 'hav1ng', 'hlgh', 'purity,', 'while', 'the', 'methyllithlum', 'reactions', 'lead', 'to', 'partial-', ',ly', 'racemized', 'methylnlcotines.', 'For', 'the', 'methylllthium', 'reactions', '*', 'Tjthe', 'recovered', 'nicotine', '1s', 'often', 'nearly', 'optically', 'pure._', 'Independ—_', '3', 'ently,', '(S)', '(', ')', '6—methylnicot1ne', 'was', 'treated', 'w1th', 'methyllithium', '”“vand', 'was', 'recovered', 'w1th', 'full', 'opt1ca1', 'act1v1ty', 'These', 'results', 'i;;#suggest', 'that', 'the', 'loss', 'of', 'optical', 'activ1ty', 'in', 'the', 'methylnlcotines', '?in', 'the', 'methylllthlum', 'reactions', 'occurs', 'during', 'the', 'reactlon', 'itself', ".:’»;.'", '‘»\\‘.', '.', "_'", '_;', 'P', 'o', 'and', 'is', 'not', 'due', 'to', 'either', 'racemization', 'of', 'the', 'starting', 'material', 'or', 'My‘', '‘gto', 'subsequent', 'racemlzatlon', 'of', 'the', 'initially', 'formed', 'product']