- A flexible approach to hexahydronaphthalene-1-carboxylates
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A flexible approach to hexahydronaphthalene-1-carboxylates based on the Favorskii rearrangement of 1,1-dichloro bicyclo[5.4.0]undec-5-en-2-ones has been devised. 1,1-Dichloro bicyclo[5.4.0]undec-5-en-2-ones can be prepared from readily available cyclohexa
- Li, Zhi,Alameda-Angulo, Celia,Quiclet-Sire, Béatrice,Zard, Samir Z.
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experimental part
p. 9844 - 9852
(2012/02/05)
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- A convenient two-step procedure for the synthesis of di- and trisubstituted α-nitroalkenes from tertiary β-nitro alcohols
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Treatment of tertiary β-nitro alcohols I, obtained by addition of lithium α-lithionitronates to ketones, with acetic anhydride followed by 1 equivalent of potassium methoxide or t-butoxide, according to the nature of R2, gives α-nitroalkenes II
- Ferrand,Schneider,Gerardin,Loubinoux
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p. 4329 - 4336
(2007/10/03)
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- Regioselective replacement of nitro or sulfonyl group in cyclic α-(nitroalkyl)- or α-(phenylsulfonylalkyl)enones by nucleophiles
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Cyclic α-(nitroalkyl)enones and α-(phenylsulfonylalkyl)enones undergo regioselective substitution of the nitro group by relatively soft sulfur, nitrogen and carbon nucleophiles.
- Tamura, Rui,Katayama, Hitoshi,Watabe, Ken-Ichiro,Suzuki, Hitomi
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p. 7557 - 7568
(2007/10/19)
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- Facile Synthesis of Allylic Nitro Compounds by N,N-dimethylethylenediamine-Catalyzed Condensation of Aliphatic and Alicyclic Ketones with Primary Nitroalkanes
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Aliphatic as well as alicyclic ketones condense with primary nitroalkanes in the presence of N,N-dimethylethylenediamine (1) to give allylic nitro compounds selectively in good to excellent yields without forming α-nitro olefins.Condensation of 2-alkanones and 2-methylcyclopentanone with nitromethane produces the products of thermodynamic control, while the product of kinetic control is obtained from 2-methylcyclohexanone.Propiophenone, an aromatic ketone, reacted with nitromethane in a way analogous to aliphatic ketones to give the corresponding allylic nitro product.A reaction mechanism to account for the exclusive formation of allylic nitro compounds is proposed.Some allylic nitro compounds thus obtained are converted into α,β-unsaturated aldehydes and ketones by treatment with sodium methoxide and then TiCl3 in buffered solution.
- Tamura, Rui,Sato, Masahiro,Oda, Daihei
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p. 4368 - 4375
(2007/10/02)
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