Structures and Reactions of Certain Sulfur-Ylides

Nozaki, H.; Takaku, Masaaki; Tunemoto, Daiei; Yamamoto, Yasusi; Kondo, Kiyoshi

doi:10.1246/nikkashi1948.88.1

Nippon Kagaku Zasshi

1967

DOI: 10.1246/nikkashi1948.88.1

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Structures and Reactions of Certain Sulfur-Ylides

H. Nozaki¹,

Masaaki Takaku²,

Daiei Tunemoto³

et al.

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Cited by 10 publications

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“…The nature of the bonding in sulfonium ylides has been elucidated by chemical studies.2-5 Several reviews of the literature are available. [6][7][8] (1) Part II in this series: John P. Schaefer and Karen Walthers, Tetrahedron, 27, 5289 (1971). This work represents a portion of the dissertation of L. L. Reed presented to the Graduate College of the University of Arizona in partial fulfillment of the requirements for the Ph.D. degree.…”

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confidence: 99%

Molecular rearrangements. XXVIII. Nitrous acid deamination of 3-exo-phenyl-3-hydroxy- and 3-endo-phenyl-3-hydroxy-2-endo-norbornylamines

Collins¹,

Glover²,

Eckart³

et al. 1972

J. Am. Chem. Soc.

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The title compounds, labeled both with deuterium and with carbon-14, have been subjected to nitrous acid deamination in acetic acid-sodium acetate solution. The yields of products have been determined by gpc, by isotope dilution, by liquid column chromatography, or by all three methods. The mechanistic implications of the data-namely that the "memory effects'' can be explained by counterion control and that the classical carbonium ion intermediates survive several 1,2 shifts-are discussed in detail. It is concluded either that "hot" carbonium ions are not necessary to explain the results, or that they must be redefined. a multiplicity of products (by comparison with the corresponding solvolyses). By definition,7 then, "hot" carbonium ions should have "lost most if not all of their sizzle"8 after a single hydride shift or Wagner-Meerwein rearrangement.

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mentioning

confidence: 99%

Molecular rearrangements. XXVIII. Nitrous acid deamination of 3-exo-phenyl-3-hydroxy- and 3-endo-phenyl-3-hydroxy-2-endo-norbornylamines

Collins¹,

Glover²,

Eckart³

et al. 1972

J. Am. Chem. Soc.

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Studies of acyl and thioacyl isocyanates—XII

1973

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Preparative and structural studies on certain sulphur-ylides

et al. 1967

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Structures and Reactions of Certain Sulfur-Ylides

Cited by 10 publications

References 0 publications

Molecular rearrangements. XXVIII. Nitrous acid deamination of 3-exo-phenyl-3-hydroxy- and 3-endo-phenyl-3-hydroxy-2-endo-norbornylamines

Molecular rearrangements. XXVIII. Nitrous acid deamination of 3-exo-phenyl-3-hydroxy- and 3-endo-phenyl-3-hydroxy-2-endo-norbornylamines

Studies of acyl and thioacyl isocyanates—XII

Preparative and structural studies on certain sulphur-ylides

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