84333-98-2Relevant articles and documents
Polyhalogenated Bicycloocta-1,5,7-trienes, XI. - Preparation and Reactions of Bicycloocta-1,3,5-trien-7,8-diyl Sulfates
Roedig, Alfred,Ganns, Eva Maria,Ganns, Rainer
, p. 1982 - 1994 (2007/10/02)
The cyclic sulfates 4a, d and e were prepared from 1a, d and e with sulfuric acid at room temperature.At a higher temperature the diketones 3a or b are produced.Thermolysis of the sulfates at 180-200 deg C as well as acidic hydrolysis lead likewise to 3a or b.Alkaline hydrolysis, however, yields the phthalides 5a or b.Analogous reaction courses are observed with alkoholates yielding 5c, d, f, methanethiolate giving 5e, and secondary amines 8a-f.Contrary, with ammonia and primary amines the phenylglyoxylic amides 13a-f are formed.The other ring opening products 9a, b, 10, and 11 are obtained from 4a with phenolates under different conditions.In the reactions 4 -> 8 the intermediates 6 and 7 can be isolated, so that some general mechanistic interpretations are possible.
