344750-31-8Relevant articles and documents
ADDITION TO BICYCLOBUTANE DERIVATIVES. VI. STEREOCHEMISTRY OF ADDITION OF SODIUM THIOLATES TO ACTIVATED BICYCLOBUTANES
Razin, V. V.,Vasin, V. A.,Ogloblin, K. A.
, p. 2223 - 2229 (2007/10/02)
In methanol sodium methanethiolate and thiophenolate add to methyl 1-bicyclobutanecarboxylate, 3-methyl-1-bicyclobutanecarboxylate, and 1-tricycloheptanecarboxylate exclusively at the central bicyclobutane C-C bond with nucleophilic attack at the β position to the methoxycarbonyl group.Here the bicyclic substrates exhibit poorly defined cis-stereoselectivity, while the tricyclic substrate exhibits distinct trans-stereoselectivity.The effect of the nature of the activating group on the stereoselectivity of addition of the anionoid nucleophiles to the activated bicyclobutanes is discussed.