Publications [#232232] of Stephen L Craig

Journal Articles

1. Kropp, PJ; Breton, GW; Craig, SL; Crawford, SD; Durland, WF; Jones, JE; Raleigh, JS, Surface-Mediated Reactions. 6. Effects of Silica Gel and Alumina on Acid-Catalyzed Reactions, Journal of Organic Chemistry, vol. 60 no. 13 (June, 1995), pp. 4146-4152, American Chemical Society (ACS), ISSN 0022-3263 [doi]
   (last updated on 2026/01/16)

   Abstract:
   Adsorption of a variety of acids to chromatographic silica gel results in substantial enhancement of their catalytic activity–affording easily prepared, environmentally benign heterogeneous acids that are highly effective in mediating a number of processes. This was shown for the isomerization of aliene 1 and dimerization of the corresponding 1,3-diene 2; cyclization of (R)-citronellal (5), the related diester 10, and 1,5-cyclooctadiene (15); Rupe rearrangement of alkynol 18; and Friedel-Crafts cyclodehydration of alcohols 21. By contrast, commercially available Nafion-H was significantly less effective as a heterogeneous acid catalyst. Chromatographic alumina displayed enigmatic behavior, showing enhanced acidity on the adsorption of HCl but little or no acidity on the adsorption of a variety of other types of acid. The results are discussed in terms of the surface structures of silica gel and alumina. © 1995, American Chemical Society. All rights reserved.