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By Thomas Wirth, T. Wirth H. Kessler (Editor), K.N. Houk (Editor), J.-M. Lehn (Editor)

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Additional info for Topics in current chemistry, 208, Organoselenium Chemistry: Modern Developments in Organic Synthesis

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Thus, Nicolaou showed that compound 213 reacted with N-PSP 11 to form the intermediate 214 which then afforded the cyclopropane derivative 215 (Scheme 32) [109]. Further examples were reported by Herndon [110]. As indicated in Scheme 32, in the presence of tin tetrachloride, the stannane 216 was converted into the cyclopentane derivative 217. This cyclization reaction proved to be quite general with respect to a variety of substitution patterns but it appears to be restricted to the formation of three- and fivemembered ring.

58 58 59 60 61 62 63 63 64 66 67 68 Topics in Current Chemistry, Vol. 208 © Springer-Verlag Berlin Heidelberg 2000 56 4 M. Iwaoka · S. Tomoda . . . . . . . 1 Boron . . . . 2 Aluminum . . . 3 Indium . . . . 1 Silicon . . . . 2 Tin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

In the presence of an isocyanide, lithium selenocarbamidates 2 are produced, which can be trapped with butyl iodide to give the corresponding isoselenoureas 3 in good yields (Scheme 3) [5]. When the reaction is carried out under carbon monoxide atmosphere, the corresponding selenocarbamates are obtained [5]. 58 M. Iwaoka · S. 1 Use of Alkali Metals and Hydrides Reduction of diphenyl diselenide by sodium metal in refluxing THF produces copious precipitates of the salt of a benzeneselenolate anion 4 (Scheme 4 a) [6].

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