Competitive RO-6 neighboring group participation and solvent-assisted displacement with 2-(2-methoxyethoxy) ethyl tosylate

SP McManus, RM Karaman, BA Hovanes…

Index: McManus, Samuel P; Karaman, Rashid M.; Hovanes, Bruce A.; Paley, Steven M.; Harris, Milton J. Journal of Organic Chemistry, 1988 , vol. 53, # 3 p. 681 - 683

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Citation Number: 4

Abstract

Notes ri~ atives.~ These results would suggest that those derivatives may undergo hydrolysis by competitive mechanisms, giving dioxane by an 0-6 process. It is possible that some 3-OH formed via attack by water at one of the methylene carbons of the cyclic oxonium ion. In theory our NM'R experiment with 3-d2-OTs could reveal whether this occurs since the two methylene carbons are not equivalent in the deuterium-labeled tosylate. However, the ...