Electronic structure of the open forms of three-membered rings

Hayes, Edward F.; Siu, Albert K. Q.

doi:10.1021/ja00737a064

Cited by 167 publications

(103 citation statements)

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“…ASDWl is stable in a region surrounding the equilibrium flat triangular geometry. The 7r diradical character of O3 at the equilibrium geometry was reported by Hay et al (1975).…”

Section: Aswl = (U+c-)(t2+) ( T I -) ( T L + T Z -)mentioning

confidence: 68%

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

Fukutome

1981

Int J of Quantum Chemistry

294

276

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“…ASDWl is stable in a region surrounding the equilibrium flat triangular geometry. The 7r diradical character of O3 at the equilibrium geometry was reported by Hay et al (1975).…”

Section: Aswl = (U+c-)(t2+) ( T I -) ( T L + T Z -)mentioning

confidence: 68%

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

Fukutome

1981

Int J of Quantum Chemistry

294

276

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“…[23] In contrast to bicyclic ylide 16, 21 is almost planar (a 0°, 0°F conformation) [24] and therefore should possess more diradical character and be less polar than 16. [9,24,25] The heterocycle 18 is predicted to almost exclusively give ylide E-21 which lies in a relatively deep well with reasonable barriers toward formation of propan-2-ylidene [TS(E-21/24), 12.4 kcal/mol], 1-methoxyethylidene [TS(E-21/25), 7.3 kcal/ mol], and 2-(1-methoxyethoxy)propene (27) [TS(E-21/27), 7.1 kcal/mol] (start on the right side of Figure 5). Calculations at the CCSD(T) level confirm the validity of the B3LYP results but also show that the stabilities of the carbonyl ylides 21 are slightly underestimated.…”

Section: Investigation Of the Reaction Mechanismsmentioning

confidence: 99%

2‐Methoxy‐Δ³‐1,3,4‐oxadiazoline, a Multipurpose Precursor for the Generation of a Carbene, an Ylide, or a Diazo Compound

et al. 2008

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In the course of our investigation of the intermolecular reactions of foiled carbenes of the norborn-2-en-7-ylidene type, we have investigated the decomposition of methoxyoxadiazoline 1 in alcohols. Most of the reactions performed lead to products with an anti configuration confirming the participation of the double bond to the stabilization of the transition states. The thermal behavior of spirooxadiazoline 1 is quite different from the behavior of the parent 2-methoxy-2,5,5-trimethyl-∆ 3 -1,3,4-oxadiazoline. Photolysis of 1 leads to the carbene after prior formation of the diazo compound whereas thermolysis cleanly generates an extremely unstable carbonyl ylide 4 that immediately decomposes to the stabilizednucleophilic carbene 5 and methyl acetate without genera-

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“…If we are to use the definition of Hayes and Siu (12) then from the diradical we are equally likely to get closure to the cis-isomer as to the trans. This does not take into account the relative thermodynamic stabilities of the cisand trans-isomers.…”

Section: Resultsmentioning

confidence: 99%

The Racemization of trans-1,2-Divinylcyclopropane

Arai¹,

Crawford²

1972

Can. J. Chem.

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The synthesis of (-)-trans-l,2-divinylcyclopropane and the kinetics of its racemization and conversion to 1,4-cycloheptadiene, presumably through cis-l,2-divinylcyclopropane, are described. It is concluded that the ring opening is not an electrocyclic process.La synthtse du (-)-trans-divinyl-1,2 cyclopropane ainsi que la cinktique de sa rackmisation et transformation en cycloheptaditne-1,4, probablement via le cis-divinyl-1,2 cyclopropane, sont rapportkes. II en a ktk dtduit que l'ouverture du cycle n'est pas un processus blectrocyclique.

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Electronic structure of the open forms of three-membered rings

Cited by 167 publications

References 0 publications

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

2‐Methoxy‐Δ³‐1,3,4‐oxadiazoline, a Multipurpose Precursor for the Generation of a Carbene, an Ylide, or a Diazo Compound

The Racemization of trans-1,2-Divinylcyclopropane

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Electronic structure of the open forms of three-membered rings

Cited by 167 publications

References 0 publications

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions

2‐Methoxy‐Δ3‐1,3,4‐oxadiazoline, a Multipurpose Precursor for the Generation of a Carbene, an Ylide, or a Diazo Compound

The Racemization of trans-1,2-Divinylcyclopropane

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2‐Methoxy‐Δ³‐1,3,4‐oxadiazoline, a Multipurpose Precursor for the Generation of a Carbene, an Ylide, or a Diazo Compound