Premium
Structure of the cis and trans Isomers of 2,4‐Bis(diethylamino)‐1,5‐dimethyl‐1,5,2,4‐diazadiphosphorinan‐6‐one 2,4‐Disulfide
Author(s) -
Shevchenko Igor V.,
Fischer Axel,
Jones Peter G.,
Schmutzler Reinhard
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270711
Subject(s) - chemistry , bicyclic molecule , cis–trans isomerism , crystal structure , structural isomer , stereochemistry , sulfur , crystallography , organic chemistry
The 2,4‐bis(dialkylamino)‐1,5‐dimethyl‐1,5,2,4‐diazadiphos‐phorinan‐6‐ones 1a and 1b (R = CH 3 , a ; C 2 H 5 , b ) are thermally unstable and are transformed into the bicyclic species 2 when heated to 150°C (2 Torr). The reactions of 1a and 1b with elemental sulfur lead to the P , P ′‐disulfides 4a and 4b as a mixture of cis and trans isomers which are separated by column chromatography. Single‐crystal X‐ray structure determinations were conducted on compound 2 and on the cis and trans isomers of 4b . The bicyclic compound 2 is found to display crystallographic twofold symmetry. Its structure is closely similar to that of the diphenyl analogue. For the cis and trans isomers of 4 almost ideal S‐P…P‐S torsion angles are observed. The isomers adopt different ring conformations.