Synthesis of 4-substituted-3-alkoxy-3-cyclobutene-1, 2-diones

MW Reed, DJ Pollart, ST Perri, LD Foland…

Index: Reed, Michael W.; Pollart, Daniel J.; Perri, Steven T.; Foland, Lafayette D.; Moore, Harold W. Journal of Organic Chemistry, 1988 , vol. 53, # 11 p. 2477 - 2482

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Citation Number: 84

Abstract

Our preparation of cyclobutenediones 3 involves 1, 2-addition of an oreanolithium reaeent to a dialkoxvcvclobutenedione, foll0; ved by hydroly& of the &hydro&" enol ether moiety in the initially formed 4-substituted-4-hydroxy-2, 3-dialkoxycyclobutenones! The addition of a wide variety of organolithium reagents to dialkyl squaates 1 occurs rapidly (5-30 min) at-78" C in dilute THF. Generally, after quenching the reaction with 10% NH, Cl at-78" C, the mixture ...