Acknowledgment. Financial support from the National Institutes of Health through NIH Biomedical Sciences Research Support Grant No. RR-7059 is gratefully acknowledged, as is support in the form of supplies, services, and facilities made available to J.K.W. by Sobering Corp. We thank Nicolet XRD Corp. for the use of computational facilities8 and Prof. Gree Loober Spoog for helpful consultations.

en-3-ol, 88357-95-3; geranyl acetoacetate, 10032-00-5; (E)-l-(trimethylsilyl)-3-penten-2-ol, 80993-48-2; 3-methyl-l-(trimethylsilyl)-3-buten-2-ol, 80399-29-7; (E)-2-buten-l-ol, 504-61-0; 4,4dimethyl-l-penten-3-ol, 24580-44-7; 3,8-dimethyl-l,7-nonadien-3-ol, 88343-80-0; (£)-2,8-dimethyl-2,7-nonadien-l-ol, 88343-81-1; diketene, 674-82-8; (E)-4-[(trimethylsilyl)methyl]-5-hepten-2-one, 88343-83-3; 5-methyl-4-[ (trimethylsilyl)methyl] -5-hexen-2-one, 88343-85-5; 4-methyl-5-hexen-2-one, 61675-14-7; (E)-6,10-dimethyl-5,9-undecadien-2-one, 3796-70-1; (Z)-6,10-dimethyl-5,9undecadien-2-one, 3879-26-3; (£)-4-methyl-6-phenyl-5-hexen-2one, 88343-86-6; (E)-4-phenyl-5-hepten-2-one, 88343-87-7; (E)-7.7-dimethyl-5-octen-2-one, 61478-31-7; 4-(dimethylamino)pyridine, 1122-58-3; 4,8-dimethylnona-l,7-dien-3-yl acetoacetate, 88343-88-8; (£)-2,8-dimethylnona-2,7-dien-2-yl acetoacetate, 88343-89-9.

4113 Experimental SectionThe alkyl(trimethylsily1)amines and (trimethylsily1)aniline were all prepared according to the literature;' bis(trimethylsily1)amine was purchased (Fisher Scientific) and distilled prior to use. Acid chlorides were purchased (Aldrich) and checked for purity by NMR and IR spectroscopy; if necessary they were purified by distillation or recrystallization. All solvents were distilled from calcium hydride immediately prior to use. All reactions were performed under an atmosphere of dry nitrogen with the aid of a vacuum manifold.Products were characterized by 'H NMR (Varian EM 360L) and IR (Perkin Elmer 735B) spectroscopy; melting points were taken with a Fisher-Johns melting point apparatus and checked against published values, agreeing in all cases to within *3 "C. Elemental analyses were performed by Micanal of Tucson, AZ.Preparation of Monofunctional Amides. A representative procedure for reactions of this type is given here for the synthesis of N-tert-butylacetamide. A 250-mL two-necked flask equipped with a magnetic stirrer and an addition funnel was evacuated and filled with dry Nz. tert-Butyl(trimethylsily1)amine (5.81 g, 0.040 mol) was added along with 120 mL of hexane. Acetyl chloride (2.9 mL, 0.041 mol) was added dropwise to the room-temperature solution, resulting in the formation of a white precipitate; stirring was continued for 5 h. Vacuum filtration, washing with hexane to remove residual chlorotrimethylsilane, and recrystallization from isopropyl alcohol yielded 4.05 g (88%) of the product amide [mp 97-98 "C (lite7 mp 97 "C)]. Reactions of Diacid Chlorides with Alkyl(trimethy1-si1yl)amines. A. Preparation of Diamides.A typical reaction is described here for the synthesis of N,IV,iV',"-tetraethyloxamide. Oxalyl chloride (4.68 g, 0.0369 mol) in 10 mL of hexane was slowly added to diethyl(trimethylsily1)amine (10.90 g, 0.0750 mol) in 90 0022-3263 I 8 3 / 1948-4116$01.50 I O , I ,

Das Cyclohexanon (II) setzt sich mit Formaldehyd und verschiedenen Aminen in Dioxan bei Raumtemperatur zu den Mannich‐Basen (I) um.

m‐Anisaldehyde (I) is converted to the trimethylsilyl compound (III) which undergoes condensation reaction with nitromethane (IV) to give the β‐nitrostilbene (V).