1,4-DIARYLSULFONYL-1,3-BUTADIENES FROM 1,4-DIARYLSULFONYL-2-BUTYNES

References

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• All new compounds are supported by excellent elemental analysis, ultraviolet, infrared, NMR, and mass spectral data (See Table II)
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• Thyagarajan , B. S. and Wood , B. F. Jr. 1983 . 39th Southwest Regional Meeting of the ACS . Dec. 7–9 1983 . Paper no. 324
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• The geometries of the diene systems of 2 and 3 were determined by 13C and 1H NMR spectroscopy. The symmetrical compound 2 gave 13C spectrum of 7 lines, while the unsymmetrical compound 3 produced 12 lines with coincidental chemical shifts of the methyl carbons and two olefinic carbons. Differentiation between the two possible symmetrical structures (E. E or Z,Z) was accomplished by spin simulation of the observed centrosymmetric AA'BB' pattern of the diene systems. The vA - vB = 32 Hz, J AB = + 13 Hz, J BB' = − 10 Hz, and J AB = + 1.5 Hz parameters reproduced the actual spectrum, with the J AB value being consistent only with the proposed E,E geometry. Additional confirmation for the E,Z isomer was obtained by comparison8 of its proton NMR data with those of compound 11. We thank Professor Fuchs P. L., Department of Chemistry, Purdue University, for generously providing us with NMR data as well as a sample of 11
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