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Cleavage of α-(phenylthio)alkylboranes with N-chlorosuccinimide. A convenient route to monothioacetals and acetals
作者:Abel Mendoza、Donald S. Matteson
DOI:10.1016/s0022-328x(00)84872-x
日期:1978.8
sulfur. Under free radical conditions, α-(phenylthio)alkaneboronic esters are cleaved to α-(phenylthio)alkyl chlorides by either N-chlorosuccinimide or sulfuryl chloride. Pinacol phenylthio(triphenylstannyl)methaneboronate with sulfuryl chloride yielded (phenylthio)dichloromethane, without any evidence of selectivity between carbontin and carbonboron bond cleavage.
可以通过两种不同的同源方法轻松制备的α-(苯硫基)烷基硼烷,由N-氯代琥珀酰亚胺在温和的碱性甲醇中脱硼,生成单硫缩醛或与过量的试剂二甲基乙缩醛。硼酸酯和三烷基硼烷都会发生反应,后者反应的速度要快得多。该反应对于硫取代的烷基硼烷基团是特定的,表明初始氯化发生在硫上。在自由基条件下,α-(苯硫基)链烷硼酸酯被N-氯代琥珀酰亚胺或磺酰氯裂解为α-(苯硫基)烷基氯。频哪醇苯硫基(三苯基锡烷基)甲烷硼酸酯与硫酰氯反应生成(苯硫基)二氯甲烷,没有任何证据表明碳锡和碳硼键裂解之间具有选择性。
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MANDAI, TADAKATSU;HARA, KIYOMI;NAKAJIMA, TSUKASA;KAWADA, MIKIO;OTERA, JUN+, TETRAHEDRON LETT., 1983, 24, N 45, 4993-4996
作者:MANDAI, TADAKATSU、HARA, KIYOMI、NAKAJIMA, TSUKASA、KAWADA, MIKIO、OTERA, JUN+
DOI:——
日期:——
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FORTES, C. C.;FORTES, H. C.;GONCALVES, D. C. R. G., AN. ACAD. BRAS. CIENC., 1983, 55, N 3, 235-243
作者:FORTES, C. C.、FORTES, H. C.、GONCALVES, D. C. R. G.
DOI:——
日期:——
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RAWAL, VIRESH, H.;AKIBA, MITSUO;CAVA, M. P., SYNTH. COMMUN., 1984, 14, N 12, 1129-1139
作者:RAWAL, VIRESH, H.、AKIBA, MITSUO、CAVA, M. P.
DOI:——
日期:——
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Rawal, Viresh H.; Akiba, Mitsuo; Cava, Michael P., Synthetic Communications, 1984, vol. 14, # 12, p. 1129 - 1140
作者:Rawal, Viresh H.、Akiba, Mitsuo、Cava, Michael P.
DOI:——
日期:——