Sulfur as a regiochemical control element. Synthesis of 2-alkoxy (acyloxy)-3-alkyl (aryl) thiobuta-1, 3-dienes
…, WC Vladuchick, AJ Bridges
Index: Trost,B.M.; Vladuchick,W.C.; Bridges,A.J. Journal of the American Chemical Society, 1980 , vol. 102, p. 3554
Full Text: HTML
Citation Number: 45
Abstract
Abstract: The internal competition between substituents in the 2, 3 positions of a diene-one being a sulfur and the other an oxygen substituent-is discussed. To examine this question, a general approach to 2-alkoxy (acyloxy)-3-alkyl (aryl) thiobuta-I, 3-dienes has been developed. Bromocyclobutanone undergoes displacement with sulfur nucleophiles without competing rearrangements of the benzylic acid type. These compounds have been 0- ...
Related Articles:
Use of silyloxydienes in synthesis. Total syntheses of the sesquiterpene (.+-.)-seychellene
[Jung,M.E.; Mccombs,C.A.; Takeda,Y. Journal of the American Chemical Society, 1981 , vol. 103, p. 6677]
[Arstad, Erik; Barrett, Anthony G. M.; Hopkins, Brian T.; Koebberling, Johannes Organic Letters, 2002 , vol. 4, # 11 p. 1975 - 1977]
Lewis acid catalyzed Diels-Alder reactions of two useful dienyl phosphate esters
[Liu, Hsing-Jang; Feng, Waiseng Martin; Kim, Jeung Bea; Browne, Eric N. C. Canadian Journal of Chemistry, 1994 , vol. 72, # 10 p. 2163 - 2175]