2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF5 Groups: A Synthetic and Structural Study

详细信息    查看全文

• 作者：Guoxiong Hua ; Junyi Du ; Alexandra M. Z. Slawin ; J. Derek Woollins
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：May 2, 2014
• 年：2014
• 卷：79
• 期：9
• 页码：3876-3886
• 全文大小：567K
• 年卷期：v.79,no.9(May 2, 2014)
• ISSN：1520-6904

文摘

A series of new 2,4-diaryl-1,3-chalcogen azoles having pentafluorosulfanyl SF₅ functional groups has been prepared by means of the two-component cyclization of the selenoamide or thioamide with 伪-bromoketones. The selenoamides or thioamides were obtained from the reaction of Woollins鈥?reagent or Lawesson鈥檚 reagent with 4-pentafluorosulfanylbenzonitrile, followed by hydrolysis with water. All new compounds were characterized by ¹H, ¹³C, ⁷⁷Se, ¹⁹F NMR spectroscopy, and accurate mass measurement. X-ray crystal structure analysis of the selenoamide, thioamide, and 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles reveal that the selenoamide and thioamide have very similar structural features along with similar intermolecular interactions such as the 蟺鈥撓€ stacking and the weak N鈥揌路路路E (E = S or Se) hydrogen bonding. The 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles show the newly formed five-membered N(1)鈥揅(2)-E(3)-C(4)鈥揅(5) ring is either perfectly planar (and coplanar with two peripheral aryl ring planes) or near-planar. The 蟺鈥撓€ intermolecular interactions and the weak C鈥揌路路路蟺 and C鈥揌路路路X (X = Br, F, O) hydrogen bonding are discussed in the cases of 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles.