Search results for "Styrene oxide"
showing 2 items of 22 documents
Fate of Epdxides
1982
One of the most important reactions of epoxides appears to be the covalent binding to DNA which can lead to mutagenicity and is strongly suspected to be the primary lesion ultimately leading to initiation of cancer (Miller and Miller, 1974; Oesch, 1973; Jerina and Daly, 1974; Sims and Grover, 1974; Heidelberger, 1975; Gelboin et al., 1972). This review first describes structure-activity relationships for the mutagenicity of some epoxides and then outlines some findings on the metabolic control of the concentration of such epoxides by a number of enzymes.
Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
2008
Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.