Kotoji Sugahara

Reaction of α-trifluoromethylacrylic acid with various unsaturated Grignard reàgents

Abstract The reactions of 2-(trifluoromethyl)propenoic acid ( I ) with unsaturated Grignard reagentshave been examined. Vinylmagnesium bromide with I gave 2-difluoromethylene-4-pentenoicacid ( II ) and analogous acids were obtained from propenyl and butenyl magnesiumhalides. The iodolactonization of II gave 2-difluoromethylene-4-iodomethyl-γ-lactone ( III ).2-Monofluoromethylene-4-penten-1-ol ( IV ) was obtained by the reduction of II with lithiumaluminium hydride.

Products from the reaction of fatty acids with ketones and their characteristic properties as cutting fluids additives

Hydroxy acids were synthesized in good yields from ketones and fatty acids by the use of lithium naphthalene in the presence of diethylamine. For example, from cyclohexanone and undecylenic acid (I), 2-(1-hydroxy-1-cyclohexyl)-10-undecenoic acid (III) was obtained in 92% yield. Hydroxy acids were treated withp-toluenesulphonic acid to give corresponding unsaturated fatty acids. From the reaction of (III), 2-(1-cyclohexenyl)-10-undecenoic acid (IV), a 3,4-unsaturated acid was obtained (yield 59%). Corrosion and lubricity tests for these products as water-based cutting fluid additives were carried out. We have found that triethanolamine salts of 2-cyclohexenyl and 2-hydroxycyclohexyl fatty acids showed effective rust-inhibiting and antiwear properties for water-based cutting fluids.

Synthesis of β-Lactams from 1-Citronellal

ABSTRACT This paper concerns a preparative method of β-lactam formation using N-[(3R)-3, 7-dimethyl-6-octen-1-ylidene]-N-cyclohexylamine [I] derived from 1-citronellal. The reaction of [I] with ethyl bromoacetate in the presence of zinc gave a β-lactam 4-[(2R)-2, 6-dimethyl-5-hepten-1-yl]-(1-cyclohexyl)azetidin-2-one [II]. Instead of β-lactam for-mation, N-[(3R)-3, 7-dimethyl-1, 6-octadien-1-yl]-N-cyclohexyl-2-methylpropionamide[III] was obtained from the reaction of [I] with isobutyryl chloride and triethylamine.