Accession Number : ADA133697

Title :   Macrocycles Containing Tin. Syntheses of Symmetrical Macrocycles Containing Two or Four Diphenylstanna Units.

Descriptive Note : Technical rept.,

Corporate Author : TEXAS A AND M UNIV COLLEGE STATION DEPT OF CHEMISTRY

Personal Author(s) : Newcomb,Martin ; Azuma,Yutaka

PDF Url : ADA133697

Report Date : 07 Oct 1983

Pagination or Media Count : 28

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.

Descriptors :   *Cyclic compounds, *Tin compounds, *Synthesis(Chemistry), Organometallic compounds, Phenyl radicals, Stannates, Bromine compounds, Magnesium compounds, Alkanes, Chlorides, Lithium, Chemical reactions, Purification, Chromatography, Nuclear magnetic resonance, Spectroscopy, Molecular weight

Subject Categories : Organic Chemistry
      Atomic and Molecular Physics and Spectroscopy

Distribution Statement : APPROVED FOR PUBLIC RELEASE