Preparation and Characterization of New C2-and C1-Symmetric Nitrogen, Oxygen, Phosphorous, and Sulfur Derivatives and Analogs of TADDOL. Part II

TADDOL (=a,a,a',a'-Tetraaryl-1,3-dioxolane-4,5-dimethanol) and the corresponding dichloride are converted to TADDAMINs (=(4S,5S)-2,2,N,N'-tetramethyl-a,a,a',a'-tetraphenyl-1,3-dioxolan-4,5-dimethanamines) (Scheme 2) and ureas, 1215, and to TADDOP derivatives with seven-membered O?P?O ester rings (Schemes 3 and 4). Cl/P-Replacement via the Michaelis?Arbuzov reaction (Scheme 7) on mono- and dichlorides, derived from TADDOL, are described. It was not possible to obtain phosphines with the P-atom attached to the benzhydrylic C-atom of the TADDOL skeleton (Schemes 6 and 7). The X-ray crystal structures (Figs. 1 and 2) of ten of the more than 30 new TADDOL derivatives are discussed. Full experimental details are presented.