Structure of Radicals Produced by γ-Radiolysis. Part 3. Radicals Derived from Adamantane, Adamantyl Derivatives, and Diamantane

HYFANTIS, GEORGE J. JUN.; Ling, A. Campbell

doi:10.1139/v74-189

Cited by 11 publications

(2 citation statements)

References 11 publications

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“…sane") can also be used for the same purpose, Results and Discussion although it offers no advantages over adamantane ~i~~~~~~~~ as an isolation matrix (2).…”

Section: Methodsmentioning

confidence: 99%

Mass spectrometry of diamantane and some adamantane derivatives

Waltman¹,

Ling²

1980

Can. J. Chem.

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The mass spectrometric fragmentation of adamantane, adamantane-d6, diamantane, 1- and 2-adamantanol, and 3,5,7-trimethyl-1-adamantanol has been re-examined, and new data for diamantane and 3,5,7-trimethyl-1-adamantanol are presented in more detail. Metastable peak data have been used to support potential fragmentation pathways. Simple statistical considerations applied to peak intensity data seem to indicate that ionization occurs at the primary bridgehead in both adamantane and diamantane, and that loss of a primary hydrogen is favored over loss of a secondary hydrogen atom.

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“…sane") can also be used for the same purpose, Results and Discussion although it offers no advantages over adamantane ~i~~~~~~~~ as an isolation matrix (2).…”

Section: Methodsmentioning

confidence: 99%

Mass spectrometry of diamantane and some adamantane derivatives

Waltman¹,

Ling²

1980

Can. J. Chem.

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confidence: 99%

ChemInform Abstract: SIGMATROPIC AND ELECTROCYCLIC REACTIONS OF BICYCLO(3.2.0)HEPTADIENYL RADICALS, 3‐QUADRICYCLANYL RADICALS, AND 7‐NORBORNADIENYL RADICAL

Sustmann¹,

Brandes²,

Lange³

et al. 1985

Chemischer Informationsdienst

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The rearrangement of matrix-isolated organic radicals with bicyclo[3.2.0]heptadienyl structure (2, 5, lla,b), 3-quadricyclanyl structure (16,26,27), and of 7-norbornadienyl radical 15 is studied. Final rearrangement products are radicals with tropylium structure. 16, 26, and 27 isomerize to radicals with bicyclo[3.2.0]heptadienyl skeleton before electrocyclic ring opening to tropylium radicals takes place. 7-Norbornadienyl radical 15 is the least stable radical on the C,-hypersurface. Free radical rearrangements of bicyclic model systems under conditions of long life time have been the subject of several electron spin resonance investigations and a part of the work presented here has been published in preliminary form'-3). The purpose of studying rearrangements of matrix isolated free radicals is to demonstrate that sofar unknown radical reactions can take place with activation energies similar to reactions of comparable ionic species. Eventually this may lead to the application of such reactions in the synthesis of complex organic molecules.In solution bicyclo[3.2.0]hepta-2,6-diene (1) is converted by hydrogen abstraction of an allylic hydrogen atom with photolytically generated tert-butoxy radicals to bicyclo[3.2.0]heptadienyl radical (2). Its ESR spectrum can be interpreted in terms of four different coupling constants. Due to the molecular symmetry hy-0 VCH Verlagsgesellschaft mbH, D

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Rearrangements of free radicals, XI. Sigmatropic and electrocyclic reactions of bicyclo[3.2.0]heptadienyl radicals, 3‐Quadricyclanyl radicals, and 7‐norbornadienyl radical

et al. 1985

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The rearrangement of matrix‐isolated organic radicals with bicyclo[3.2.0]heptadienyl structure (2, 5, 11a,b), 3‐quadricyclanyl structure (16, 26, 27), and of 7‐norbornadienyl radical 15 is studied. Final rearrangement products are radicals with tropylium structure. 16, 26, and 27 isomerize to radicals with bicyclo[3.2.0]heptadienyl skeleton before electrocyclic ring opening to tropylium radicals takes place. 7‐Norbornadienyl radical 15 is the least stable radical on the C7‐hypersurface. Sigmatropic 1,2‐vinyl shifts in bicyclo[3.2.0]heptadienyl radicals could not be observed. Substituents do not influence the rearrangement behaviour.

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Structure of Radicals Produced by γ-Radiolysis. Part 3. Radicals Derived from Adamantane, Adamantyl Derivatives, and Diamantane

Cited by 11 publications

References 11 publications

Mass spectrometry of diamantane and some adamantane derivatives

Mass spectrometry of diamantane and some adamantane derivatives

ChemInform Abstract: SIGMATROPIC AND ELECTROCYCLIC REACTIONS OF BICYCLO(3.2.0)HEPTADIENYL RADICALS, 3‐QUADRICYCLANYL RADICALS, AND 7‐NORBORNADIENYL RADICAL

Rearrangements of free radicals, XI. Sigmatropic and electrocyclic reactions of bicyclo[3.2.0]heptadienyl radicals, 3‐Quadricyclanyl radicals, and 7‐norbornadienyl radical

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