A 'head-to-tail' type cyclodextrin dimer, where C-3 of one cyclodextrin and C-6 of the other are linked by a disulfide bond, is synthesized using 2,2'-dipyridyl disulfide, which is widely applicable to the preparation of other dimers.
A mixture of the title ditosylates was prepared by the reaction of β-cyclodextrin with dibutyltin oxide and tosyl chloride. Each ditosylate was isolated by reversed-phase column chromatography and the structure was assigned on the basis of conversion into a known compound or hydrolysis with Taka amylase A.
Received M a y 13, 19922A,6x-Bis-0-(mesitylsulfonyl)-@-cyclodextrins (X = A-G) were prepared by the reaction of 2-O-(mesitylsul-fony1)-8-cyclodextrin with mesitylenesulfonyl chloride in pyridine. All regioisomers were isolated and their structures determined.Bifunctionalization of cyclodextrins has attracted much attention with respect to the construction of artificial en-The reaction of (trimethylsily1)vinyl selenide 1 and (trimethylsi1yl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoseledively. The reaction of 1 and 3a-c with SnCb was quenched either with EhN to give cyclobutanes 4a-c or with H20 to give acylsilanes 1 la-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.
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