Diels-Alder reactions of N-silyloxy 1-azadienes

…, LS Stelzer, M Ahmadian, J Haddad, JA Scherschel

Index: Behforouz, Mohammad; Gu, Zhengxiang; Stelzer, Lindsay S.; Ahmadian, Mohammad; Haddad, Jalal; Scherschel, John A. Tetrahedron Letters, 1997 , vol. 38, # 13 p. 2211 - 2214

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Citation Number: 28

Abstract

Novel 1-(t-butyldimethylsilyloxy)-1-aza-1, 3-butadienes 1 and 2 are prepared by the reaction of O-(t-butyldimethylsilyloxy) hydroxylamine with methyl vinyl ketone and methacrolein, respectively. Azadienes 1 and 2 through sharing of oxygen nonbonding electrons are activated and thus their Diels-Alder reactions with a number of halobenzoquinones, napthoquinones and N-phenylmaleimide regiospecifically give low to good yields of ...