86236-67-1Relevant academic research and scientific papers
FACTORS CONTROLLING C=C VS. C=O ATTACK IN CYCLOADDITION OF A 1,3-DIENE TO AN AMBIDENT DIENOPHILE. DIELS-ALDER REACTION OF 2-PHENYL-Δ2-PYRROLINE-4,5-DIONES
Sano, Takehiro,Toda, Jun,Tsuda, Yoshisuke
, p. 356 - 359 (2007/10/02)
The cycloaddition using an enone as a dienophile is on a balance with the normal C=C attack (ene-addition) and the unusual C=O attack (one-addition) of a diene.Steric hindrance on the C=C (caused by such phenomena as restricted free rotation of the substituent on C=C) retards the C=C attack, thus increasing the ratio of one-addition.Lewis acids greatly increase not only the reactivity of C=O but also the ratio of one-addition.KEYWORDS --- 1-methoxy-3-trimethylsilyloxybutadiene; Diels-Alder reaction; dioxopyrroline; ambident dienophile; ene-addition; one-addition; steric hindrance; Lewis acid
