cheminform abstract: 1,3-dipolar cycloadditions. part 115. cycloadditions of thiocarbonyl ylides...

2000 cycloaddition reactions cycloaddition reactions O 0070 10 - 048 1,3-Dipolar Cycloadditions. Part 115. Cycloadditions of Thiocarbonyl Ylides with N-Sulfinylamines. — The cycloaddition of thiobenzophenone S-methylide with N-sulfinylamines (III) provides 1,3,4-dithiazolidine S-oxides (IV) in good yield. Similar reaction of thiocarbonyl ylide derived from spiroth- iadiazoline (V) gives corresponding 1,3,4-dithiazolidine S-oxides (VI). However, reaction of ylide derived from (V) with N-sulfinyltosylamine gives the adduct to the S=O bond, oxadithiolane 2-tosylimide (VIIb), as the major product. Cycloaddition mechanisms, especially for the unique formation of oxadithiolane (VIIb), are discussed. — (HUISGEN, ROLF; MLOSTON, GRZEGORZ; POLBORN, KURT; Heteroat. Chem. 10 (1999) 7, 662-669; Inst. Org. Chem., Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany; EN) 1

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Page 1: ChemInform Abstract: 1,3-Dipolar Cycloadditions. Part 115. Cycloadditions of Thiocarbonyl Ylides with N-Sulfinylamines

2000 cycloaddition reactions

cycloaddition reactionsO 0070

10 - 0481,3-Dipolar Cycloadditions. Part 115. Cycloadditions of ThiocarbonylYlides with N-Sulfinylamines. — The cycloaddition of thiobenzophenoneS-methylide with N-sulfinylamines (III) provides 1,3,4-dithiazolidine S-oxides(IV) in good yield. Similar reaction of thiocarbonyl ylide derived from spiroth-iadiazoline (V) gives corresponding 1,3,4-dithiazolidine S-oxides (VI). However,reaction of ylide derived from (V) with N-sulfinyltosylamine gives the adductto the S=O bond, oxadithiolane 2-tosylimide (VIIb), as the major product.Cycloaddition mechanisms, especially for the unique formation of oxadithiolane(VIIb), are discussed. — (HUISGEN, ROLF; MLOSTON, GRZEGORZ;POLBORN, KURT; Heteroat. Chem. 10 (1999) 7, 662-669; Inst. Org. Chem.,Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany; EN)

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