Macrocycles Containing Tin. Syntheses of Symmetrical Macrocycles Containing Two or Four Diphenylstanna Units.
TEXAS A AND M UNIV COLLEGE STATION DEPT OF CHEMISTRY
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The syntheses of macrocycles containing two diphenylstanna moieties, cyclo-Ph2SnCH2n-2 1, n 4, 5, 6, 8, 10, 12, and four diphenylstanna moieties, cyclo-Ph2SnCH2n -4 2, same n, are reported. Alpha, omega-bis Bromomagnnesioal-kanes reacted with Ph3SnC1 to give alpha, omega-bistriphenylstannylalkanes which upon treatment with HBr gave alpha, omega-bis bromodiphenylstannylalkanes 4. Compounds 4 reacted with the corresponding chain length alpha, omega-bisbromomagnesioalkanes 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 C1CH2 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.
- Organic Chemistry
- Atomic and Molecular Physics and Spectroscopy