4′ Diphenylphosphino and bromo derivatives of 10-phenyl-1,4,7-trithia-10-azacyclododecane 4-R-C6H4N(CH2CH2S) 2CH2CH2SCH2CH2

Article abstract of DOI:10.1080/10426509708043504

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.

Full text of DOI:10.1080/10426509708043504

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Phosphorus, Sulfur, and Silicon and
the Related Elements
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4′ DIPHENYLPHOSPHINO AND
BROMO DERIVATIVES OF 10-
PHENYL-1,4,7-TRITHIA-10-AZA-
CYCLODODECANE 4-R- C6H4
N(CH2CH2S)2CH2CH2SCH2CH2
Lance R. Hoover a , Travis Pryor a , Jeremy A. Weitgenant a ,
Peter E. Williams a , Bruce N. Storhoff a & John C. Huffman b
a Department of Chemistry , Ball State University , Muncie,
IN, 47306, USA
b Molecular Structure Centre, Department of Chemistry ,
Indiana University , Bloomington, IN, 47405, USA
Published online: 04 Oct 2006.
To cite this article: Lance R. Hoover , Travis Pryor , Jeremy A. Weitgenant , Peter E.
Williams , Bruce N. Storhoff & John C. Huffman (1997) 4′ DIPHENYLPHOSPHINO AND
BROMO DERIVATIVES OF 10-PHENYL-1,4,7-TRITHIA-10-AZA-CYCLODODECANE 4-R- C6H4
N(CH2CH2S)2CH2CH2SCH2CH2 , Phosphorus, Sulfur, and Silicon and the Related Elements, 122:1,
155-166, DOI: 10.1080/10426509708043504
To link to this article: http://dx.doi.org/10.1080/10426509708043504
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