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A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride

✍ Scribed by Paul E. Morgan; Ray McCague; Andrew Whiting


Book ID
104261677
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
180 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


Tosyl cyanide is activated by titanium(W) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo-and regio-spec~cally adds to certain alkenes to provide ~chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide [J-hydroxysulfoxides


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A novel synthesis of 2,3-dihydro-1H-thie
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A series of cyclic sulfonium ylides 4a-h reacted with titanium(IV) chloride in the presence of triethylamine to give the corresponding fused 2,3-dihydro-1H-thieno [3,4-b]pyrroles 5a-h, via a ring opening and recyclization. In contrast, treatment of compounds 4a, 4b, 4e and 4f with titanium(IV) chlor