Macrocycles containing tin. Syntheses of symmetrical macrocycles containing two or four diphenylstanna units
Macrocycles containing tin. Syntheses of symmetrical macrocycles containing two or four diphenylstanna units
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含有锡的大环化合物。
DOI：
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发表时间：
1984
期刊：
影响因子：
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通讯作者：
M. Newcomb
中科院分区：
文献类型：
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作者：
Y. Azuma;M. Newcomb
摘要：本文报道了含两个二苯基锡原子的大环化合物cyclo-（Ph_2Sn（CH_2）n-）_2（1，n = 4，5，6，8，10，12）和含四个二苯基锡原子的大环化合物cyclo-（Ph_2Sn（CH_2）n（-）_4（2，n相同）的合成。α，ω-双（溴镁）烷与Ph 3SnCl反应得到α，ω-双（三苯基甲锡烷基）烷，其经HBr处理得到α，ω-双（溴二苯基甲锡烷基）烷（4）。化合物4与相应链长的α，ω-双（溴镁）烷烃反应得到1和2。或者，通过将4转化为二锂试剂（7），使其与α，ω-二溴烷烃反应，获得良好的产率1（n = 4，5，6，8）。通过首先用Cl（CH 2）MgBr处理4以得到二氯化物，然后在第二步中使其与7反应，获得了2（n = 4，5，6）的良好产率。大环化合物和几种合成中间体的纯化通过制备反相色谱法进行。大环产物通过核磁共振谱、分子量测定和元素分析进行了表征。
Abstract : The syntheses of macrocycles containing two diphenylstanna moieties, cyclo-(Ph2Sn(CH2)n-)2 (1, n = 4, 5, 6, 8, 10, 12), and four diphenylstanna moieties, cyclo-(Ph2Sn(CH2)n (-)4 (2, same n), are reported. Alpha, omega-bis (Bromomagnnesio)al-kanes reacted with Ph3SnC1 to give alpha, omega-bis(triphenylstannyl)alkanes which upon treatment with HBr gave alpha, omega-bis (bromodiphenylstannyl)alkanes (4). Compounds 4 reacted with the corresponding chain length alpha, omega-bis(bromomagnesio)alkanes to give 1 and 2. Alternatively, good yields of 1 (n = 4, 5, 6, 8) were obtained by converting 4 to dilithium reagents (7) which were allowed to react with alpha, omega-dibromoalkanes. Good yields of 2 (n = 4, 5, 6) were obtained by first treating 4 with C1(CH2) MgBr to give dichlorides which were then allowed to react with 7 in a second step. Purifications of the macrocyles and several synthetic intermediates were effected by preparative reverse phase chromatography. The macrocyclic products were characterized by NMR spectroscopy, molecular weight determinations and elemental analyses.