Pa. Duspara et al., Twisted amides: Synthesis and structure of 1,6-dipivaloyl-3,4,7,8-tetramethyl-2,5-dithioglycoluril, ORG LETT, 3(4), 2001, pp. 495-498
The 1,6-dipivaloyl derivative of 3,4,7,8-tetramethyl-2,5-dithioglycoluril (
6) was prepared and the crystal structure determined by X ray diffraction;
6 is a twisted amide in which severe ring strain and nonbonded interactions
compel both pivaloyl groups to twist dramatically out of the ring plane. T
he amide oxygen atoms point in opposite directions with respect to the mean
plane through the glycoluril core, and the bridgehead methyl groups are fo
rced out of the symmetric syn geometry (eta = 30.5 degrees). The structure
of 7, a rearrangement product generated during synthesis of 6, was also det
ermined by single crystal X ray diffraction.