Abstract
4-Br-C6H4N(CH2CH2S)2CH2CH2SCH2SCH2CH2 and 4-Ph2P-C6H4N(CH2CH2S) 2CH2CH2SCH2CH2 have been synthesized and characterized. The former cyclododcane has been obtained from the reaction between 4-BrC6H4N(CH2CH2Cl)2 and S(CH2CH2SH)2 in N,N-dimethylformamide containing Cs2CO3. The latter has been obtained from the former by way of a low temperature lithium-bromine exchange reaction (butyllithium) that provided the carbanion which was subsequently reacted with chlorodiphenylphosphine. In regard to characterization, X-ray methods have been used to study the former (P21, a = 8.356(3) Å, b = 12.325(5) Å, c = 16.012 (7). β = 100.81, Z = 4), and two crystallographically independent molecules were found. In both molecules, the nitrogen atoms are nearly planar with short N-C(sp2) bond lengths, and, second, the sulfur atoms are in exodenate positions. For the phosphine, a 31P signal was observed at -7.1 ppm, and this peak position was considered to be indicative of a structure involving a planar nitrogen atom.