Chemistry of the l,3?5-Triaza-2-phosphorin-4,6-diones, Part XI*. Base-Catalyzed Addition Reactions of 2-Oxo-2-hydro-l,3>5-trimethyl-l,3>5-triaza-2/4-phosphorine-4,6-dione to the C=N Double Bond of 3-Thiazoline Heterocycles

Ion N ed aa, T hom as K au k o ra ta, P e te r G. Jo n esa, R e in h a rd S ch m u tz le r* * a, H ara ld G rö g e rh, Jü rgen M arten sb a Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329. D-38023 Braunschweig b Fachbereich Chemie der Universität Oldenburg. Postfach 2503. D-26111 Oldenburg Dedicated to Professor R. D. Chambers on the occasion o f his 60th birthday Z. Naturforsch. 51b, 1486-1493 (1996); received January 22, 1996 2-Oxo-2-hydro-l,3,5-trimethyl-1.3.5-triaza-2A4-phosphorine-4.6-dione. 3-Thiazolines, Base Catalysis. X-Ray. NMR Spectra The base-catalyzed reaction of 2-oxo-2-hydro-1.3,5-trimethyl-l,3,5-triaza-2/l4-phosphorine4,6-dione (1) and of its trimethylsiloxy phosphorus(III) derivative (10) with various 3-thiazolines (2 -5 ) via five different pathways is described. In all cases, the corresponding 3-thiazoline adducts were formed. The different routes are compared with regard to reaction condi­ tions and yields. In the reaction of 1 with 5,5-dimethyl-2-isopropyl-3-thiazoline (3) two diastereomers of 7 were formed, as established by 'H , 13C and 31P NMR spectroscopy. The structures of the products 6 and 8 were confirmed by X-ray analysis; the thiazolidine rings display a twist conformation through the sulfur atom. The molecules are linked via inversion centres by hydrogen bonds of the form N -H --0 = C .