Get Organoselenium Chemistry: Modern Developments in Organic PDF

By Thomas Wirth (auth.), Dr. Thomas Wirth (eds.)

ISBN-10: 3540665161

ISBN-13: 9783540665168

Embarking on a brand new millennium, the e-book in arms describes the hot advancements of organsoselenium chemistry in all features. a variety of distinct scientists have contributed, with their ability and services, making this e-book a helpful resource for man made orientated natural chemists and for these, who are looking to get a primary perception into the chemistry of selenium.

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Electrophilic Selenium, Selenocyclizations 47 Scheme 40. Phenylselenyl Sulfate Catalyzed One-Pot Conversions of Dicarbonyl Compounds into Vicinal Monoprotected Tricarbonyl and Diprotected Tetracarbonyl Compounds b-Diketones 253 and b-keto esters 254, with the same procedure, were converted into the corresponding monoprotected vicinal tricarbonyl compounds 255 and 256, respectively (Scheme 40) [120]. Whenever the group linked to ketonic carbonyl was a methyl (R = Me), the diprotected vicinal tetracarbonyl compounds 257 and 258 were produced.

Mihelich ED, Hite GA (1992) J Am Chem Soc 114:7318 75. Tiecco M, Testaferri L, Santi C (1999) Eur J Org Chem 797 76. Landais Y, Planchenault D, Weber V (1995) Tetrahedron Lett 36:2987 and references cited therein 77. Landais Y, Planchenault D (1995) Synlett 1191 and references cited therein 78. Kahn SD, Pau CF, Chamberlin AR, Hehre WJ (1987) J Am Chem Soc 109:650 and references cited therein 79. Tiecco M, Testaferri L, Bagnoli L (1996) Tetrahedron 52:6811 80. Fragale G, Wirth T (1998) Eur J Org Chem 1361 81.

Under the usual conditions, the oximes 271 react with phenylselenyl sulfate to afford the nitrones 272 which react with the persulfate to give pyridine N-oxides 273 by deselenenylation and dehydrogenation [126]. Several research groups have recently investigated the asymmetric version of the catalytic one-pot selenenylation-deselenenylation sequence described above. In particular, attention was devoted to the process in which the deselenenylation occurs with elimination. These experiments are simply carried out by replacing the diphenyl diselenide with a chiral diselenide and are suggested to proceed through a sequence of reaction steps similar to those proposed for the diphenyl diselenide by Tomoda [122] or by Tiecco [116] and indicated in the Schemes 36 and 37.

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Organoselenium Chemistry: Modern Developments in Organic Synthesis by Thomas Wirth (auth.), Dr. Thomas Wirth (eds.)


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