4'-DIPHENYLPHOSPHINO AND BROMO DERIVATIVES OF 10-PHENYL-1,4,7-TRITHIA-10-AZA-CYCLODODECANE 4-R-C6H4N(CH2CH2S)(2)CH2CH2SCH2CH2

Citation
Lr. Hoover et al., 4'-DIPHENYLPHOSPHINO AND BROMO DERIVATIVES OF 10-PHENYL-1,4,7-TRITHIA-10-AZA-CYCLODODECANE 4-R-C6H4N(CH2CH2S)(2)CH2CH2SCH2CH2, Phosphorus, sulfur and silicon and the related elements, 122, 1997, pp. 155-166
Citations number
19
ISSN journal
10426507
Volume
122
Year of publication
1997
Pages
155 - 166
Database
ISI
SICI code
1042-6507(1997)122:<155:4ABDO1>2.0.ZU;2-J
Abstract
4-Br-C6H4N(CH2CH2S)(2)CH2CH2SCH2CH2 and 4-Ph2P-C6H4N(CH2CH2S)(2)CH2CH2 SCH2CH2 have been synthesized and characterized. The former cyclododca ne has been obtained from the reaction between 4-BrC6H4N(CH2CH2Cl)(2) and S(CH2CH2SH)(2) in N,N-dimethylformamide containing Cs2CO3. The lat ter has been obtained from the former by way of a low temperature lith iumbromine exchange reaction (butyllithium) that provided the carbanio n which was subsequently reacted with chlorodiphenylphosphine. In rega rd to characterization, X-ray methods have been used to study the form er (P2(1), a = 8.356(3) Angstrom, b = 12.325(5) Angstrom, c = 16.012 ( 7), beta = 100.81, Z = 4), and two crystallographically independent mo lecules were found. In both molecules, the nitrogen atoms are nearly p lanar with short N-C(sp(2)) bond lengths, and, second, the sulfur atom s are in exodenate positions. For the phosphine, a P-31 signal was obs erved at -7.1 ppm, and this peak position was considered to be indicat ive of a structure involving a planar nitrogen atom.