Determination of the photolytic decomposition pathways of benzylchlorodiazirine by C60 probe technique

Ishitsuka, Midori O.; Enoki, Haruka; Nikawa, Hidefumi; Wakahara, Takatsugu; Tsuchiya, Takahiro; Akasaka, Takeshi; Liu, Michael T. H.

doi:10.1016/j.tetlet.2006.11.145

Cited by 8 publications

(2 citation statements)

References 16 publications

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“…The ORTEP diagram of 3 is presented in Figure 5 with the selected bond lengths and angles collected in Table 1. The cage C-C bond lengths of the addition sites are C1-C9: 1.623(2) Å and C21-C40: 1.6282(19) Å, which fall within the range of the corresponding values reported for the crystal structures of methano-derivatives of C 60 [5,[21][22][23][24][25][26][27][28][29][30][31][32][33]. It is noteworthy that these C-C bond lengths are longer than those of the reported siliranes [34][35][36][37][38][39][40][41][42], except for rare examples such as 3-(hydroxydimesitylsilyl)-1,1-dimesityl-2,2-bis(trimethylsilyl)-1-silirane [43].…”

Section: Synthesis Of Bis-silylene Adductsupporting

confidence: 82%

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Kako,

Kai,

Yasui

et al. 2024

Beilstein J. Org. Chem.

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The addition reaction of C60 with silylene 1, a silicon analog of carbene, yielded the corresponding bis-adduct 3. The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a silirane (silacyclopropane) derivative of fullerenes. Electrochemical measurements confirmed that the redox potentials of 3 are shifted cathodically compared to those of the parent mono-adduct 2. Density functional theory (DFT) calculations provided the basis for the electronic properties of compound 3.

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Section: Synthesis Of Bis-silylene Adductsupporting

confidence: 82%

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Kako,

Kai,

Yasui

et al. 2024

Beilstein J. Org. Chem.

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“…Kinetically, both the RIES and a carbene olefin complex (COC) pathway account for the nonlinearity of the plots of [addition]/[rearr] versus [TME]. When photolysis of 165 was conducted in the presence of C 60 , formation of [6,6] closed methanofullerene 168 (31%) and 167 (57%, E / Z ratio is 4:1) was achieved, although no fulleroid was detected . This is consistent with the very low quantum yield for diazo formation reported by Platz and co-workers.…”

Section: Carbene Addition To Empty Fullerenessupporting

confidence: 81%

Carbene Additions to Fullerenes

2013

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CONTENTS 1. Introduction 7209 2. Carbene Addition to Empty Fullerenes 7210 2.1. Dihalocarbenes 7210 2.1.1. Dihalocarbene Additions to C 60 7210 2.1.2. Dihalocarbene Additions to C 70 7212 2.1.3. Dihalocarbene Additions to Fullerene Fragments 7213 2.2. Decomposition of Diazo Compounds 7215 2.2.1. Thermolysis of Diazo Compounds 7215 2.2.2. Photolysis of Diazo Compounds 7223 2.2.3. In-Situ Generation of Diazo Compounds 7223 2.2.4. Isomerization of Fulleroids to Methanofullerenes 7228 2.3. Decomposition of Diazirines 7233 2.3.1. Chemical Probe 7233 2.3.2. Photoaffinity Labeling 7237 2.3.3. Fullerene Sugars 7237 2.3.4. Addition−Elimination Reaction 7238 2.4. Decomposition of Diazonium Salts 7238 2.5. Alkoxycarbenes 7238 2.6. Vinylcarbenes 7239 2.7. Basic Treatment of Malonates in the Presence of Iodine 7240 2.8. Photolysis of Benzocyclobutenediones 7240 2.9. α-Ketocarbenes 7240 2.10. Fischer Carbene Complexes 7241 2.11. Heterocyclic Carbenes 7242 2.12. Zwitterionic Intermediates 7244 2.13. Si and Ge Analogues of Carbenes 7244 2.13.1. Silylene Addition to C 60 7244 2.13.2. Silylene Addition to C 707245 2.13.3. Germylene Addition to C 60 7245 3. Carbene Additions to Endohedral Metallofullerenes 7245 3.1. Endohedral Metallofullerenes 7245 3.2. M@C 2v (9)-C 82 7246 3.2.1. Photolysis of Diazirines 7246 3.2.2. Thermolysis of Diazomethanes 7248 3.2.3. In-Situ Generation of Diazo Compounds 7248 3.2.4. Metal-Catalyzed Reactions 7248 3.2.5. Zwitterionic Intermediates 7248 3.3. M@C s (6)-C 82 7249 3.4. M 2 @I h (7)-C 80 7249 3.4.1. Photolysis of Diazirines 7249 3.4.2. In-Situ Generation of Diazo Compounds 7251 3.5. M 2 @D 3h (5)-C 78 7251 3.5.1. Photolysis of Diazirines 7251 3.5.2. Thermolysis of Diazirines 7252 3.6. M 2 @D 2 (10611)-C 72 7252 3.7. M 3 N@I h( 7)-C 80 7252 3.7.1. In-Situ Generation of Diazo Compounds 7252 3.7.2. Silylenes 7253 3.8. Sc 2 C 2 @C 3v (8)-C 82 7254 3.9. Sc 2 C 2 @C 2v (5)-C 80 7254 3.10. Sc 3 C 2 @I h (7)-C 80 7255 3.11. Li@C 60 7255 4. Concluding Remarks 7256 Author Information 7257 Corresponding Author 7257 Notes 7257 Biographies 7257 Acknowledgments 7258 References 7258

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Radical reaction and Photoreaction

Maeda

Nagase

Akasaka

2021

Handbook of Fullerene Science and Technology

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Determination of the photolytic decomposition pathways of benzylchlorodiazirine by C60 probe technique

Cited by 8 publications

References 16 publications

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Carbene Additions to Fullerenes

Radical reaction and Photoreaction

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Determination of the photolytic decomposition pathways of benzylchlorodiazirine by C60 probe technique

Cited by 8 publications

References 16 publications

Two-fold addition reaction of silylene to C60: structural and electronic properties of a bis-adduct

Two-fold addition reaction of silylene to C60: structural and electronic properties of a bis-adduct

Carbene Additions to Fullerenes

Radical reaction and Photoreaction

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Product

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Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct