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Preparation and Characterization of New C 2 ‐ and C 1 ‐Symmetric Nitrogen, Oxygen, Phosphorous, and Sulfur Derivatives and Analogs of TADDOL. Part II
Author(s) -
Pichota Arkadius,
Gramlich Volker,
Bichsel HansUlrich,
Styner Thomas,
Knöpfel Thomas,
Wünsch Ralf,
Hintermann Tobias,
Schweizer W. Bernd,
Beck Albert K.,
Seebach Dieter
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200147
Subject(s) - chemistry , nitrogen , sulfur , nitrogen atom , oxygen atom , oxygen , crystal structure , medicinal chemistry , organic chemistry , molecule , group (periodic table)
TADDOL (= α , α , α′ , α′ ‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol) and the corresponding dichloride are converted to TADDAMINs (=(4 S ,5 S )‐2,2, N , N′ ‐tetramethyl‐ α , α , α′ , α′ ‐tetraphenyl‐1,3‐dioxolan‐4,5‐dimethanamines) ( Scheme 2 ) and ureas, 12 – 15 , and to TADDOP derivatives with seven‐membered OPO ester rings ( Schemes 3 and 4 ). Cl/P‐Replacement via the MichaelisArbuzov 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.