Three-Membered Ring Systems

Lapinsky, David J.

doi:10.1016/b978-0-08-100017-5.00003-0

Cited by 5 publications

(1 citation statement)

References 227 publications

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“…The three-membered rings are also highly versatile building blocks, frequently involved in the synthesis of natural compounds and incorporated into the molecular scaffold of numerous bioactive products and pharmaceuticals [7,8].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

et al. 2019

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Small ring heterocycles, such as epoxides and aziridines, are present in several natural products and are also highly versatile building blocks, frequently involved in the synthesis of numerous bioactive products and pharmaceuticals. Because of the potential for increased efficiency and selectivity, along with the advantages of environmentally benign synthetic procedures, multicomponent reactions (MCRs) have been explored in the synthesis and ring opening of these heterocyclic units. In this review, the recent advances in MCRs involving the synthesis and applications of epoxides and aziridines to the preparation of other heterocycles are discussed emphasizing the stereoselectivity of the reactions.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

et al. 2019

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Reversible Photothermal Isomerization of Carborane‐Fused Azaborole to Borirane: Synthesis and Reactivity of Carbene‐Stabilized Carborane‐Fused Borirane

2017

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Af ully reversible photothermal isomerization between carborane-fused trigonal-planar azaborole (darkpurple) and tetrahedral borirane (pale-yellow) has been observed, leading to the isolation and structural characterization of the first example of carborane-fused borirane.DFT calculations indicate that the azaborole is thermodynamically more stable than the borirane by 11.2 kcal mol À1 ,a nd the energy barrier for the thermal conversion from azaborole to borirane is 35.5 kcal mol À1 .The reactivity studies show that the BÀC(cage) bond in borirane can be broken in the reaction with CuCl, HCl, or elemental sulfur. Scheme 1. Photothermal transformations of four-coordinate organoboranes.Scheme 2. Photothermal isomerization between 1 and 2.

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Reversible Photothermal Isomerization of Carborane‐Fused Azaborole to Borirane: Synthesis and Reactivity of Carbene‐Stabilized Carborane‐Fused Borirane

2017

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A fully reversible photothermal isomerization between carborane-fused trigonal-planar azaborole (dark-purple) and tetrahedral borirane (pale-yellow) has been observed, leading to the isolation and structural characterization of the first example of carborane-fused borirane. DFT calculations indicate that the azaborole is thermodynamically more stable than the borirane by 11.2 kcal mol , and the energy barrier for the thermal conversion from azaborole to borirane is 35.5 kcal mol . The reactivity studies show that the B-C(cage) bond in borirane can be broken in the reaction with CuCl, HCl, or elemental sulfur.

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Three-Membered Ring Systems

Cited by 5 publications

References 227 publications

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Reversible Photothermal Isomerization of Carborane‐Fused Azaborole to Borirane: Synthesis and Reactivity of Carbene‐Stabilized Carborane‐Fused Borirane

Reversible Photothermal Isomerization of Carborane‐Fused Azaborole to Borirane: Synthesis and Reactivity of Carbene‐Stabilized Carborane‐Fused Borirane

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