Macrocycles Containing Tin. Syntheses of Symmetrical Macrocycles Containing Two or Four Diphenylstanna Units.
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 07, 1983
- Accession Number
- ADA133697
Entities
People
- Martin Newcomb
- Yutaka Azuma
Organizations
- Texas A&M University