- Ru-CATALYZED OXIDATION OF SUBSTITUTED ACETYLENES TO α-KETO ESTERS AND α-KETO AMIDES WITH IODOSYLBENZENE
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Oxidation of alkynyl ethers and -amines with iodosylbenzene in presence of Ru-catalysts affords α-keto esters and α-keto amides in 44-84percent yield.These conversions can also be effected with RuO4.
- Mueller, Paul,Godoy, Jose
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- 5,6,7-Trimethylocta-2,5-dien-4-one - A suspected odorant with surprising olfactory properties
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5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.
- Kraft, Philip,Denis, Caroline,Eichenberger, Walter
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p. 2363 - 2369
(2007/10/03)
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- A Simple, One-Pot Synthesis of 1-Alkoxy-1-alkynes and 1-Alkoxy-1-alkyn-3-ols
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The title compound are prepared by a high yield, one-pot reaction using readily available chloroacetaldehyde dialkyl acetals as starting materials.The reaction is initiated by sodium amide and the intermediate acetylide anion thus produced, reacts readily with a variety of electrophiles such as alkyl halides, carbonyl compounds or water to produce the desired products.
- Stalick, Wayne M.,Hazlett, Robert N.,Morris, Robert E.
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p. 287 - 290
(2007/10/02)
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