Reoelv& ir USA 30 October 1975; received in UK for publication 20 Ilevtier 1975) h the foregoing paper'we described the efficient metallation and alkylation of N, N-dimethylhydrazones (DMH'S) and also effective and mild cleavage of DMH's to carbonyl compounds. This Letter is primarily concerned with reactions of metsllated DMH's which lead to a wide variety of polyfunctional molecules. I. P-Hydroxycarbonyl Compounds. o-Lithiated DMH's undergo 1,2-addition to aldehydes and ketones to form p-hydroxy DMH's in generally high yield. 2 The process may be typified by the sequence L+J. 2-Pentanone DMH Q) was metallated' with n-butyllithium (1 equiv) in THF at -78" for 20 min, 1 equiv of crotonaldehyde (2) was added and after 3 hr at -78" and 12 hr warming to 0", neutralization with acetic acid and extractive workup (CH2C12 -H20) afforded the hydroxy DMH 3, homogeneous by tic and pmr analysis, in >98% yield. Treatment directly with sodium periodate in methanol at pH 7 and isolation as previously described afforded 7-nonen-4-on-6-ol (5) in 798% yield (pure by pmr and tic analysis). Short-path distillation (70" and 0.05 mm) was accomplished with no appreciable loss of material giving distilled $ in -195% yield overall from 2. 3 Dehydration of 4, with methanesulfonyl chloride-triethylamine furnished after isolation and distillation (50", 0.1 mm) 85% of pure trans. trams-5,7-nonadiene-4-one (2).