Two novel ten-membered ring compounds: 1,2,5,8-dithiadiazecine-6,7-diones

Abstract

The structures of two new ten-membered ring compounds, 3,4,5,8,9,10-hexamethyl-1,2,5,8-dithiadiazecine-6,7(5H,8H)-dione (I) and ll,14-dimethyldibenzo[c,f]-Acta Crystallographica Section C

Crystal and molecular structure of novel 10‐membered ring compound: 10‐Chloro‐1,7‐ditosyl‐8‐phenyl‐4,1,7‐benzoxadiazecine

“…This breaking down of the ring symmetry is caused by the introduction of the aromatic bond C(5)-C(6) and by the presence of small heteroatoms: the trigonal N(l) and N(2) nitrogen atoms, and the oxygen O(5) in the 10-membered ring. The asymmetric conformations of 10-membered rings in 1,2,5,8-dithiadiazecine-6,7-diones, as detected by X-ray crystallography in the solid state and by NMR spectroscopy in solution, were reported by Yamaguchi et al [18].…”

Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)-1,2,5,8-Dithiadiazecine-6,7(5H,8H)-dione Series

“…Display of the 11 (3 Z ,9 Z )-1,2,5,8-dithiadiazecine-6,7­(5 H ,8 H )-dione derivatives reported in the literature: 4 , − 5 , 6 , , 7 , , 8 , , 9 , , 10 , , 11 , 12 , 13 , and 14 …”

“…If truth be told, some clear evidence of the chirality in these series was already available from the reported single-crystal X-ray structure determination or in some cases from 1 H NMR spectra. Single-crystal X-ray structure determination has been the preferred method to characterize the unfamiliar (3 Z ,9 Z )-1,2,5,8-dithiadiazecine-6,7­(5 H ,8 H )-dione skeleton. ,,,, Inspection of CIF files from the Cambridge database indicates that in all cases except one, two enantiomers could be clearly recognized in the cell while asymmetric conformations were mentioned for two compounds . The exception, which is even more appealing, is compound 11 , which crystallized in a P 2 1 2 1 2 1 chiral group indicative of the probable occurrence of a conglomerate …”

“…Display of the eleven (3Z,9Z)-1,2,5,8-dithiadiazecine-6,7(5H,8H)-dione derivatives reported in literature. 4 [8][9][10][11][12] , 5 13 ,6 9,11 , 7 9,11 , 8 9,11 , 9 10,11 , 10 9,11 , 11 14 , 12 15 , 13 16 and 14. 17 They mostly appeared in relation with the synthesis of diazadithiafulvalene derivatives resulting from the dimerization of the carbene ensuing from the basic treatment of 2-unsubstituted thiazolium or benzothiazolium salts.…”

“…8,9,11,13,14 Inspection of Cif files from the Cambridge database indicates that in all cases except one, two enantiomers could be clearly recognized in the cell while asymmetric conformations were mentioned for two compounds. 10 The exception, which is even more appealing, is for compound 11 which crystallized in a P2 1 2 1 2 1 chiral group indicative of the probable occurrence of a conglomerate. 14 1 H NMR provided another obvious proof of the chirality of some of the literature samples which presented diastereotopic methylenic protons in ethyl or benzyl groups at room temperature.…”