- Preparation and Some Reactions of Benzazetidines
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Photolysis of sultams (3) lead to benzazetidines (1) via quinonemethane imine intermediates which can be trapped by dienophiles.
- Lancaster, Michael,Smith, David J. H.
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- Thermal switchability of N-chelating hoveyda-type catalyst containing a secondary amine ligand
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An investigation of aza analogues of the popular Hoveyda-Grubbs catalyst containing a secondary amine ligand is presented, proving the crucial impact of steric as well as electronic factors on the catalyst's stability and performance. The issue of latency in the reactivity profile of studied catalysts is examined, followed by structural and application studies.
- Zukowska, Karolina,Szadkowska, Anna,Pazio, Aleksandra E.,Wo?niak, Krzysztof,Grela, Karol
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experimental part
p. 462 - 469
(2012/04/23)
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- Asymmetric synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with an N-magnesio arylamine
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The synthesis of pipecolic acid and homopipecolic acid derivatives was developed from ω-(2-aminophenyl)-1-chloroalkyl p-tolyl sulfoxides by treatment with i-PrMgCl. An intramolecular nucleophilic substitution reaction of a magnesium carbenoid with an N-magnesio arylamine is the key step of this reaction. Proline and pipecolic acid derivatives were also synthesized from ω-(arylamino)-1-chloroalkyl p-tolyl sulfoxides by the same chemistry. Starting from enantiomerically pure (1S,RS)-1-chloro-3-[2-(N-methylamino)phenyl]propyl p-tolyl sulfoxide, enantiomerically pure (R)-pipecolic acid derivative was obtained. The intramolecular nucleophilic substitution reaction of the magnesium carbenoid with N-magnesio arylamine was proven to take place with inversion of the carbenoid carbon. The stereochemistry of these reactions is also discussed.
- Mitsunaga, Shintaro,Ohbayashi, Tohru,Sugiyama, Shimpei,Saitou, Takahito,Tadokoro, Makoto,Satoh, Tsuyoshi
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experimental part
p. 1697 - 1708
(2009/12/06)
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- A new synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with N-magnesio arylamine as the key reaction
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A new synthesis of pipecolic acid and homopipecolic acid derivative was accomplished from 1-chloroalkyl p-tolyl sulfoxides having a 2-aminophenyl group at the ω-position by treatment with i-PrMgCl via the intramolecular reaction of magnesium carbenoid wit
- Ohbayashi, Tohru,Mitsunaga, Shintaro,Satoh, Tsuyoshi
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p. 7829 - 7833
(2008/03/11)
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- Ortho-Vinylation reaction of anilines
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N-Alkylanilines and anilines are vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N.
- Yamaguchi, Masahiko,Arisawa, Mieko,Hirama, Masahiro
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p. 1399 - 1400
(2007/10/03)
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- Regiochemistry of Radical Cyclisations (6-exo/7-endo and 7-exo/8-endo) of N-(o-Alkenylphenyl)-2,2-dichloroacetamides
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N--2,2-dichloroacetamides, when treated with 2.2 mol-equiv. of Bu3SnH in the presence of a catalytic amount of azoisobutyronitrile, gave quinolin-2(1H)-one (6-exo closure) and/or 2H-1-benzazepin-2-one (7-endo closure) systems.In gene
- Sato, Tatsunori,Ishida, Satoshi,Ishibashi, Hiroyuki,Ikeda, Masazumi
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p. 353 - 359
(2007/10/02)
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- Pyrolyses of o-Alkoxy- and o-Alkylthio-N-Allylanilines and of Some Related O- and S-Allyl Compounds
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The o-substituted allyl compounds (1)-(12) have been pyrolysed in order to generate aminyl, phenoxyl, and thiophenoxyl radicals with adjacent substituents.In all cases, products are formed by intramolecular hydrogen transfer from the substituent to the radical centre.This process may be followed by rearrangement to give an aldehyde, by heteroatom extrusion to give an alkene, or by ring formation to give five-membered ring heterocycles (Scheme 1, routes A, B1, and B2 respectively.The distribution of products formed by each route is dependent both on the nature of the o-substituent, and on the nature of the initial radical.
- Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
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p. 1885 - 1890
(2007/10/02)
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