Phosphorus, Sulfur and Silicon and the Related Elements p. 155 - 166 (1997)
Update date:2022-09-26
Topics:
Hoover, Lance R.
Pryor, Travis
Weitgenant, Jeremy A.
Williams, Peter E.
Storhoff, Bruce N.
Huffman, John C.
4-Br-C6H4N(CH2CH2S) 2CH2CH2SCH2CH2 and 4-Ph2P-C6H4N(CH2CH 2S)2CH2CH2SCH2CH 2 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) A, b = 12.325(5) A, 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.
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