Tin-directed Baeyer-Villiger and Beckmann fragmentations

…, MA Scialdone, CR Johnson

Index: Bakale, Roger P.; Scialdone, Mark A.; Johnson, Carl R. Journal of the American Chemical Society, 1990 , vol. 112, # 18 p. 6729 - 6731

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Citation Number: 15

Abstract

Reaction conditions: The j3-tributylstannyl oxime in CH2CI2 (ca. 0.2 M) was treated with pyridine (4 eqiv) and SOClz (2 equiv) at 0 OC for OS-2.0 h followed by aqueous workup. group is a powerful directing influence, overcoming even the high propensity of anti aryl and tert-alkyl groups to migrate in a normal Beckmann rearrangement proce~ s.'~ These Beckmann fragmentations are especially clean and facile; tin-containing byproducts ...