ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Substance X, one of the three compounds obtained upon heating 5, 6-endo-epoxy-hexamethyl-bicyclo[2.2.0]hex-2-ene (11) and previously postulated by Klaus et al. [10] to be 5-acetyl-pentamethyl-bicyclo[2.1.0]pentene (9), is now shown to be hexamethyl-2-oxabicyclo[3.2.0]-hepta-3, 6-diene (10) by reinterpretation and supplementation of the spectral data and by ozonization of the dihydro derivative 16, which yields 1-acetoxy-2-acety-1-1, 2, 3, 4-tetramethyl-cyclo-butane (17). It is concluded that the Claisen equilibrium in this system lies entirely on the side of the enol ether 10; even drastic LiAIH4 conditions cannot force a reversal (10 → 9). Tetracyanoethylene adds to the enolic double bond of 10 to form the cyclo-adduct 19.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19710540610
