Bis(triphenylmethyl) peroxide

Glidewell, C.; Liles, David C.; Walton, David J.; Sheldrick, George M.

doi:10.1107/s0567740879003976

Cited by 39 publications

(20 citation statements)

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“…A BOORh moiety resulted from the reaction of a Rh‐peroxo with a boronic acid displays a trigonal boron,8c with the BO distance shorter (1.400(2) Å) and the OO distance longer (1.497(1) Å) than the above, likely because of the stronger interaction between O and three‐coordinate boron. The B‐O‐O angle (106.9(1)°) is similar to the C‐O‐O angle (107.5(2)°) in bis(triphenylmethyl)peroxide 11 …”

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confidence: 55%

Dioxygen Reactivity with a Ferrocene–Lewis Acid Pairing: Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane

Henthorn

Agapie

2014

Angew Chem Int Ed

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Ferrocenes, which are typically air‐stable outer‐sphere single‐electron transfer reagents, were found to react with dioxygen in the presence of B(C6F5)3, a Lewis acid unreactive to O2, to generate bis(borane) peroxide. Although several Group 13 peroxides have been reported, boron‐supported peroxides are rare, with no structurally characterized examples of the BO2B moiety. The synthesis of a bis(borane)‐supported peroxide anion and its structural and electrochemical characterization are described.

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confidence: 55%

Dioxygen Reactivity with a Ferrocene–Lewis Acid Pairing: Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane

Henthorn

Agapie

2014

Angew Chem Int Ed

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“…The OÀO bond length (149.2 pm) corresponds to standard values. [2,5,6,[9][10][11] Another compound (4) was formed as the main component when 1·2 OEt 2 was treated with a larger excess (7 equivalents) of tert-butyl hydrogen peroxide [Eq. (3)].…”

Section: (O)]mentioning

confidence: 99%

Reducing GaH and GaC Bonds in Close Proximity to Oxidizing Peroxo Groups: Conflicting Properties in Single Molecules

Uhl

Halvagar

Claesener

2009

Chemistry A European J

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Treatment of [Li(H(2)Ga{CH(SiMe(3))(2)}(2))]2 OEt(2) (12 OEt(2)) with two equivalents of tert-butyl hydrogen peroxide, H-O-O-CMe(3), afforded the organogallium peroxide [({(Me(3)Si)(2)HC}(2)Ga(OH)(OOCMe(3))Li)(2)] (3), which possesses oxidizing peroxo groups in close proximity to reducing Ga-C bonds. The lithium atoms of the dimeric formula units are coordinated by both oxygen atoms of the peroxides and by two hydroxo groups. The cleavage of the Ga--C bond was not observed, even when an excess of H-O-O-CMe(3) was applied. Instead, the adduct [{(Me(3)Si)(2)HC}(2)Ga(OH)(OOCMe(3))(2)Li(2)(HOOCMe(3))] (4) was isolated, which has an intact H-O-O-CMe(3) molecule terminally attached to lithium. A similar structural motif was found for the compound [(LiOOCMe(3))(2)(HOOCMe(3))(2)] (5). The trihydrido gallanate [Li(H(3)Ga-{CH(SiMe(3))(2)})]OEt(2) (2) yielded the unique peroxide [({(Me(3)Si)(2)HC}--Ga(H)(OOCMe(3))(2)Li)(2)] (6) under similar conditions that possesses Ga-C and even more reactive Ga-H bonds beside peroxo groups. It decomposed at room temperature by the insertion of oxygen atoms into the Ga-H bonds and the formation of [({(Me(3)Si)(2)HC}-Ga(OH)(OCMe(3))(OOCMe(3))Li)(2)] (7), which was isolated in a low yield. Further decomposition gave the complete degradation of all peroxo groups with the formation of a relatively complicated Li(4)Ga(4)O(8) cage (8).

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“…X-ray diffraction determined structures [8,9] show nonbonded H···C and C···C interactions between the two trityl groups, which are partially released by widening the central bond angle C(sp 3 )-X-C(sp 3 ) to the values 1208 (X = CH 2 , S) or 1288 (X = O). [10] The molecular dynamics of a more congested bis-(hexa-tert-butyl) derivative have been described as a crankshaft motion rather than slippage. The ditrityl peroxide molecule in the crystal shows a planar anti arrangement of the CÀOÀOÀC bond system (torsion angle a = 1808).…”

Section: Introductionmentioning

confidence: 99%

“…The ditrityl peroxide molecule in the crystal shows a planar anti arrangement of the CÀOÀOÀC bond system (torsion angle a = 1808). [10] The molecular dynamics of a more congested bis-(hexa-tert-butyl) derivative have been described as a crankshaft motion rather than slippage. [11] Ditrityl disulfide shows a nonplanar arrangement of the CÀSÀSÀC bond in the crystal (torsion angle a = 1108).…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Interactions of Trityl Groups

et al. 2014

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Trityl group, Tr, is a molecular dynamic rotor of which the conformation and helicity depend on other groups in the close vicinity. Interactions with another covalently linked Tr group and with other substituents are analyzed in terms of transfer of chirality to the trityl group. Two trityl groups in a molecule can mutually interact at a distance of two, three, or five bonds. Despite its size, a Tr group attached to a cyclohexane or cyclopentane ring through an oxygen or nitrogen atom adopts either an axial or equatorial position, depending on additional stabilizing interactions, such as hydrogen bonding.

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Bis(triphenylmethyl) peroxide

Cited by 39 publications

References 1 publication

Dioxygen Reactivity with a Ferrocene–Lewis Acid Pairing: Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane

Dioxygen Reactivity with a Ferrocene–Lewis Acid Pairing: Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane

Reducing GaH and GaC Bonds in Close Proximity to Oxidizing Peroxo Groups: Conflicting Properties in Single Molecules

Intramolecular Interactions of Trityl Groups

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