Reactivity of 13, 13-Dibromo-2, 4, 9, 11-tetraoxadispiro [5.0. 5.1] tridecane toward Organolithiums: Remarkable Resistance to the DMS Rearrangement†

…, M Jasinski, P Kaszynski, K Zienkiewicz…

Index: Eccles, Wendy; Jasinski, Marcin; Kaszynski, Piotr; Zienkiewicz, Katarzyna; Stulgies, Baldur; Jankowiak, Aleksandra Journal of Organic Chemistry, 2008 , vol. 73, # 15 p. 5732 - 5744

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Citation Number: 11

Abstract

Reactions of dibromocyclopropane 2a, containing two spiro-fused 1, 3-dioxane rings, with MeLi gave only the methylation products 8 and 9 even at elevated temperatures. In contrast, the cyclohexane analogue 2b treated with MeLi underwent a smooth rearrangement to bicyclo [1.1. 0] butane 11b at− 78,− 10, or+ 35° C. Treatment of 2a with PhLi gave the α-Ph anion 13 as the only product, which underwent smooth methylation with MeI to give 14. ...