Conformational analysis of 1, 3-dioxanes with sulfide, sulfoxide and sulfone substitution at C (5). Finding an eclipsed conformation in cis-2-tert-butyl-5-(tert- …

…, RA Toscano, M Soriano-Garcia…

Index: Juaristi, Eusebio; Martinez, Roberto; Mendez, Rodolfo; Toscano, Ruben A.; Soriano-Garcia, Manuel; et al Journal of Organic Chemistry, 1987 , vol. 52, # 17 p. 3806 - 3811

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Citation Number: 30

Abstract

The positions of equilibrium, established by acid catalysis, between diastereomeric cis-and trans& (tertbutylthio)-(l), 5-(tert-butylsulfinyl)-(2), and 5-(tert-butylsulfonyl)-2-isopropyl-1, 3- dioxanes (3) are reported and compared with previously published data for the 5-methylthio (4), 5-methylsulfinyl (5), and 5-methylsulfonyl (6) analogues. Although AGO values for the sulfides 1 and 4 are very similar, the difference in conformational behavior for sulfoxides 2 ...