A CONVENIENT SYNTHESIS OF OXETENE VIA [2<b>+</b>2]CYCLOADDITION REACTION UNDER MICROWAVE IRRADIATION

Longchar, Moanochet; Bora, Utpal; Boruah, Romesh C.; Sandhu, Jagir S.

doi:10.1081/scc-120014973

Cited by 12 publications

(3 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since carbonyl–alkyne [2 + 2] cycloadditions are orbital-symmetry forbidden in the ground state, either photo-irradiation or the use of a catalyst , has been established as an avenue to overcome the kinetic barriers. Nonetheless, the strained cyclic intermediate can be stabilized by electron-withdrawing substituents, which has allowed the isolation and structural characterization of many oxete derivatives. − …”

Section: Introductionmentioning

confidence: 99%

Oxophosphonium-alkyne cycloaddition reactions: reversible formation of 1,2-oxaphosphetes and six-membered phosphorus heterocycles

et al. 2020

View full text Add to dashboard Cite

While the metathesis reaction between alkynes and carbonyl compounds is an important tool in organic synthesis, the reactivity of alkynes with isoelectronic main-group R 2 EO compounds is unexplored. Herein, we show that oxophosphonium ions, which are the isoelectronic phosphorus congeners to carbonyl compounds, undergo [2 + 2] cycloaddition reactions with different alkynes to generate 1,2-oxaphosphete ions, which were isolated and structurally characterized. The strained phosphorus−oxygen heterocycles open to the corresponding heterodiene structure at elevated temperature, which was used to generate six-membered phosphorus heterocycles via hetero Diels−Alder reactions. Insights into the influence of the substituents at the phosphorus center on the energy profile of the oxygen atom transfer reaction were obtained by quantum-chemical calculations.

show abstract

Section: Introductionmentioning

confidence: 99%

Oxophosphonium-alkyne cycloaddition reactions: reversible formation of 1,2-oxaphosphetes and six-membered phosphorus heterocycles

et al. 2020

View full text Add to dashboard Cite

show abstract

“…R.C. Boruah et al described the microwave-mediated [2 + 2] cycloaddition of steroidal formyl enamides and alkynes under solvent-free conditions [97] (Scheme 25). Although much attention has been paid to the development of synthetic methodologies for oxetanes, the corresponding unsaturated analogue oxetene has received only limited interest.…”

Section: Modifications Of Steroidsmentioning

confidence: 98%

Microwave-Assisted Natural Product Chemistry

Appukkuttan

Eycken

2006

Topics in Current Chemistry

View full text Add to dashboard Cite

“…In addition, the β-formyl enamide system has been engaged in inverse electron demand DielsAlder reactions and 1,3-dipolar cycloadditions [147][148][149]. More recently, β-formyl enamides have been subjected to microwave mediated [2+2] cycloaddition reactions with alkynes to afford oxetenes in good yields [150]. The synthesis of the small and constrained oxetene carbocycle has received limited study in comparison to its corresponding saturated analog, oxetane [151][152][153][154].…”

Section: Oxetanementioning

confidence: 99%