What products at relux in nucleophilic substitution

The identity of intermediates and the roles they play has been the subject of debate. The reaction mechanism of the Mitsunobu reaction is fairly complex.

2.1 Other nucleophilic functional groups.A variation of this reaction utilizing a nitrogen nucleophile is known as a FukuyamaвЂ“Mitsunobu. This happens if the nucleophile is not acidic enough ( pK a larger than 13) or is not nucleophilic enough due to steric or electronic constraints. A common side-product is produced when the azodicarboxylate displaces the leaving group instead of the desired nucleophile. The alcohol reacts with the phosphine to create a good leaving group then undergoes an inversion of stereochemistry in classic S N2 fashion as the nucleophile displaces it. Then a solution of the nucleophile and alcohol are added together and the reaction can, and in many cases is, heated to reflux. This white, cloudy suspension is the ylide. Typical protocol is to add the phosphine and azodicarboxylate together at в€’10В вЊ, typically in THF or toluene, until a white precipitate forms.

It was discovered by Oyo Mitsunobu (1934вЂ“2003). Although DEAD and DIAD are most commonly used, there are a variety of other azodicarboxylates available which facilitate an easier workup and/or purification and in some cases, facilitate the use of more basic nucleophiles. The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD).

What products at relux in nucleophilic substitution