Posted by: Mark Foreman | February 13, 2014

Cyclohexane compounds which can and can not do a E2 reaction

Dear Reader,

Here is a compound which can not do a E2 reaction, I have created a XYZ file which can be opened in ORTEP with ease.

30
XYZ file :   trans isomer of 1-bromo-4-tertbutyl cyclohexane
C -4.123 -0.017 -0.473
C -4.253 -1.394 0.174
C -2.923 -2.143 0.174
C -1.813 -1.320 0.821
C -1.683 0.056 0.174
C -3.012 0.806 0.174
C -5.442 0.727 -0.319
C -6.438 -0.152 0.425
C -5.212 2.010 0.469
C -5.996 1.068 -1.696
Br -0.124 -2.273 0.625
H -3.869 -0.161 -1.547
H -4.595 -1.267 1.226
H -4.987 -1.987 -0.415
H -3.045 -3.093 0.741
H -2.637 -2.344 -0.882
H -2.067 -1.177 1.896
H -1.340 -0.071 -0.877
H -0.948 0.650 0.764
H -2.890 1.756 -0.393
H -3.298 1.006 1.231
H -7.403 0.392 0.538
H -6.607 -1.090 -0.150
H -6.033 -0.401 1.432
H -6.176 2.555 0.582
H -4.484 2.653 -0.076
H -4.807 1.760 1.475
H -5.302 0.690 -2.480
H -6.993 0.590 -1.823
H -6.098 2.172 -1.792

Here is a cyclohexane ring which is locked into one chair with a tert butyl group which has a bromine atom arranged with the other atoms such that it can do a E2, I have changed the atom type of the hydrogens which would be removed in the E2 to be deutrium atoms.

30
XYZ file :   cis 1-bromo-4-tertbutyl cyclohexane
C -0.047 -0.171 -0.310
C 0.037 -1.198 0.839
C 1.277 -2.100 0.724
C 2.578 -1.308 0.658
C 2.504 -0.279 -0.464
C 1.270 0.633 -0.355
C -1.336 0.708 -0.296
C -2.601 -0.183 -0.356
C -1.439 1.598 0.961
C -1.381 1.627 -1.539
Br 3.036 -0.501 2.367
H -0.086 -0.764 -1.260
H 0.053 -0.672 1.820
H -0.859 -1.861 0.844
H 1.304 -2.829 1.568
D 1.184 -2.709 -0.208
H 3.428 -2.005 0.467
H 3.436 0.335 -0.497
D 2.457 -0.819 -1.441
H 1.361 1.268 0.554
H 1.285 1.320 -1.232
H -3.525 0.425 -0.475
H -2.559 -0.892 -1.214
H -2.747 -0.774 0.574
H -2.368 2.211 0.942
H -0.589 2.310 1.040
H -1.471 0.999 1.897
H -0.597 2.416 -1.512
H -1.254 1.046 -2.480
H -2.351 2.169 -1.615
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