Download Cumulenes in Click Reactions by Henri Ulrich PDF

By Henri Ulrich

Cumulenes are natural molecules with or extra cumulative (consecutive) double bonds. Their reactions frequently continue at room temperature, without or with a catalyst, and are stereospecific, giving the response items in excessive yields – gains attribute of “click reactions”. Cumulenes in click on Reactions presents a accomplished record of cumulene platforms and their reactions, with an emphasis on their “click-like” nature. The chapters are established in response to the variety of carbon atoms within the process, together with insurance of:introduction to the chemistry of cumulenesone-carbon cumulenes: sulfines, sulfenes, thiocarbonyl S-imides, thiocarbonyl S-sulfides, and 1-aza-2-azoniaallene saltstwo-carbon cumulenes: carbon oxides, carbon sulfides, carbon nitrides (isocyanates, isothiocyanates, and carbodiimides), phosphaallenes, and diarsaallenes1,2-dicarbon cumulenes: ketenes, thioketenes, ketenimines, 1-silaallenes, 1-phosphaallenes, and different steel allenes1,3-dicarbon cumulenes: thiocarbonyl S-ylides, 2-azaallenium salts, 1-oxa-3-azoniabutatriene salts, 1-thia-3-azoniabutatriene salts, and phosphorous ylides1,2,3-tricarbon cumulenes: allenes, butatrienes, greater cumulenes and heterobutatrienesnoncarbon cumulenes: azides, triazaallenium salts, sulfur oxides, sulfur nitrides, N-sulfinylamines, sulfurdiimides, and dithionitronium cationCumulenes in click on Reactionsis a vital advisor for researchers and complicated scholars in academia and study operating in artificial natural, inorganic and bioorganic chemistry.

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Chem. 99, 1175 (1987). U. Hartwig, H. Pritzkopf and W. Sundermeyer, Chem. Ber. 121, 1435 (1988). U. Hartwig, K. Rall and W. Sundermeyer, Chem. Ber. 123, 595 (1990). H. Pritzkow, K. Rall, S. Reimann-Andersen and W. Sundermeyer, Angew. Chem. 102, 80 (1990). I. Lorenz, Angew. Chem. 90, 293 (1978). G. Opitz, Angew. Chem. 79, 161 (1967). G. Lenz and B. Zwanenburg, Houben Weyl, Vol. E11, p. 1326 (1985). G. R. Mohl, Angew. Chem. 81, 36 (1969). W. Sundermeyer, Synthesis 349, (1988). H. Pritzkow, K. Rall, S.

NR(R) CR1R2 + R3R4C R3R 4 SO2 SO2 R 1R2 N H 8 The cycloaddition reaction of sulfenes to enamines occurs readily. Linear as well as cyclic enamines react well, and primary sulfonyl chlorides react better than secondary sulfonyl chlorides. However, cycloadducts from secondary sulfonyl chlorides are obtained in excellent yield if the reaction is conducted in acetonitrile at −40 ◦ C 20 . Some of the cycloadducts rearrange to linear isomers, but this tendency is not as pronounced as in other four-membered ring cycloadducts.

R2N R2NCH CH–CH CH2 + CH2 SO2 + SO2 9 SO2 SO2 R2N 10 28 Cumulenes in Click Reactions In the reaction of N,N,N ,N -tetramethyl-1-butene-1,3-diamine with sulfene a mixture of the linear adduct 11 and cycloadducts 12 and 13 is isolated 26 . Me2NCH CH(Me)NMe2 + CH2 SO2 Me2NCH CHSO2CH CHMe + 11 Me2N Me2N + SO2 SO2 SO2 Me2N 12 13 In my earlier book I have listed the linear and the [2+2] cycloadducts obtained from sulfenes and enamines. The yields obtained were usually very high 27 . In the reaction of the enamine derived from isobutyraldehyde and sulfene, generated from diazomethane and sulfur dioxide, the [2+2] cycloadduct 14 (9–18 %) and the [2+2+2] cycloadduct 15 (2–26 %) are obtained 28 .

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