New anellated 4H-1,4,2-diazaphospholes

Betzl, Wolfgang; Hettstedt, Christina und Karaghiosoff, Konstantin (8. November 2012): New anellated 4H-1,4,2-diazaphospholes. In: New Journal of Chemistry, Bd. 37, Nr. 2: S. 481-487

Abstract

Five new anellated 4H-1,4,2-diazaphospholes including the first examples of chiral 4H-1,4,2-diazaphospholes with the (-)-menthyl substituent have been prepared by two main routes: Hantzsch type cyclocondensation of 4-phenyl-2-amino-1,3-thiazole with chloromethyl dichlorophosphine and 4+1 cyclocondensation of cycloimmonium salts derived from 4-phenyl-2-amino-1,3-thiazole and 2-aminopyridine with PCl3 and NEt3. The new compounds have been characterized by multinuclear (H-1, C-13, P-31) NMR spectroscopy. Controlled hydrolysis of 5-phenylthiazolo3,2-d]1,4,2]diazaphosphole 2a with two equivalents of water yields the corresponding zwitterionic phosphinate 9, the structure of which was elucidated by single crystal X-ray diffraction. The structure in the solid state is governed by strong N-H center dot center dot center dot O hydrogen bonding resulting in chains along the crystallographic a-axis. The chloroform molecules are integrated in the chains by weaker C-H center dot center dot center dot O bonds and C-Cl center dot center dot center dot C halogen bonds.

• Dokumententyp: Zeitschriftenartikel
• Publikationsform: Publisher's Version
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1144-0546
• Ort: THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
• Bemerkung: First publ. online. Print publ. 2013
• Sprache: Englisch