SYNTHESIS OF TETRAPHENYLSTANNACYCLOPENTADIENES (STANNOLES). 2. DERIVATIVES AND ADDUCTS OF 1,1-DIHALO-2,3,4,5-TETRAPHENYLSTANNOLES
SYNTHESIS OF TETRAPHENYLSTANNACYCLOPENTADIENES (STANNOLES). 2. DERIVATIVES AND ADDUCTS OF 1,1-DIHALO-2,3,4,5-TETRAPHENYLSTANNOLES
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四苯基锡环戊二烯（锡诺）的合成。
DOI：
10.1002/chin.198202264
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发表时间：
1982
期刊：
影响因子：
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通讯作者：
J. J. Zuckerman
中科院分区：
文献类型：
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作者：
W. A. Gustavson;L. Principe;W. Rhee;J. J. Zuckerman
SC (S) N (C2H5) 2, N (CH3) 2和P (C6H5) 2。丙酮中KF的氟化只产生X= F， Y= Br或Y= I的产物，而LiN [Si (CH3) 3] 2的锂胺化只产生X= N [Si (CH3) 3] 2， Y= Br的产物。以1,4 -二硫代- 1,2,3,4 -四苯基- 1,3 -丁二烯和（II）氯化锡为原料，通过卤化中间锡（II）锡来合成二卤斯坦诺的尝试，只得到开环产物（4-溴- 1,2,3,4 -四苯基丁二烯基）三溴化锡或（4-碘- 1,2,3,4 -四苯基丁二烯基）三碘化锡。单质氯对六苯基锡醇的轻微氯化作用也会使环碳键分裂成顺式。顺式- 1,4 -二氯- 1,2,3,4 -四苯基- 1,3 -丁二烯和二苯基锡（IV）二氯，而冰乙酸-乙酸酐混合物的作用产生四苯基呋喃和二苯基锡（IV）二醋酸酯。二卤丁酮与吡啶、2,2′-联吡啶和1,10 -菲罗啉形成中性加合物，由2,2′，2′-三吡啶生成[XSnC4 (C6H5) 4′terpy]+[X2YSnC4 (C6H5) 4]~，其中X=
SC (S) N (C2H5) 2, N (CH3) 2, and P (C6H5) 2. Fluorination by KF in acetone results in the X= F, Y= Br, or Y= I product only, and lithioamination by LiN [Si (CH3) 3] 2 yields the X= N [Si (CH3) 3] 2, Y= Br product only. Attempted synthesis of the dihalostannoles by halogenation of the intermediate tin (II) stannole from 1, 4-dilithio-l, 2, 3, 4-tetraphenyl-l, 3-butadiene and tin (II) chloride yields only the ring-opened products (4-bromo-l, 2, 3, 4-tetraphenylbutadienyl) tin tribromide or (4-iodo-l, 2, 3, 4-tetraphenylbutadienyl) tin triiodide. Even gentle chlorination of hexaphenylstannole by elemental chlorine cleaves the ringtin-carbon bonds to form cis. cis-1, 4-dichloro-1, 2, 3, 4-tetraphenyl-1, 3-butadiene and diphenyltin (IV) dichloride, while the action of a glacial acetic acid-acetic anhydride mixture yields tetraphenylfuran and diphenyltin (IV) diacetate. The dihalostannoles form neutral adducts with pyridine, 2, 2'-bipyridyl, and 1, 10-phenanthroline and the double salt [XSnC4 (C6H5) 4'terpy]+[X2YSnC4 (C6H5) 4]~ from 2, 2', 2"-terpyridine where X=