Acetolyse von endo- und exo-bicyclo-(n,1,0)-alkyl-tosylaten

Schöllkopf, Ulrich; Fellenberger, Klaus; Patsch, Manfred; Schleyer, Paul von Ragué; Su, Tingwei; Dine, George W. Van

doi:10.1016/s0040-4039(01)89813-0

Cited by 45 publications

(17 citation statements)

References 12 publications

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“…The kinetic results of Schöllkopf et al (1967;Schöllkopf, 1968) illustrate this and are shown in Table IV. For larger rings, η = 5, 6, the di-trans-(or E, 2s)-fusion is better.…”

Section: Stereochemical Aspectsmentioning

confidence: 60%

Carbocation

Sorensen¹,

Rauk²

1977

Organic Chemistry: A Series of Monographs

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“…The kinetic results of Schöllkopf et al (1967;Schöllkopf, 1968) illustrate this and are shown in Table IV. For larger rings, η = 5, 6, the di-trans-(or E, 2s)-fusion is better.…”

Section: Stereochemical Aspectsmentioning

confidence: 60%

Carbocation

Sorensen¹,

Rauk²

1977

Organic Chemistry: A Series of Monographs

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“…In 1966, Schleyer, U. Schöllkopf et al reported the solvolysis of a series of bicyclo[4.1.0]heptanes (Scheme 12 shows the two key reactions), which are completely consistent with the WÀ H rules. [230] On February 26, 1965, Wolfgang Kirmse (Figure 30) wrote [231] to Woodward that his group had determined the relative rates of solvolysis of the endo-and exo-7bromobicyclo[4.1.0]heptanes (Scheme 12; similar to those that would subsequently be published by Schleyer and Schölkopf in 1966). [232] Kirmse completed this chemistry prior to the publication of the first WÀ H paper.…”

Section: Gateway: Pericyclic Reactionsmentioning

confidence: 99%

The Many Chemists Who Could Have Proposed the Woodward‐Hoffmann Rules But Didn't: The Organic Chemists Who Discovered the Smoking Guns^[^]**

Seeman

2022

The Chemical Record

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It is a reasonable question to ask, why, as of 1965 when the five Woodward‐Hoffmann communications appeared, did no other organic chemist discover the orbital symmetry rules for pericyclic reactions? Two theoretical chemists – Luitzen Oosterhoff (in 1961) and Kenichi Fukui (in 1964) had discovered portions of the orbital symmetry rules before Woodward and Hoffmann. Why not organic chemists? Indeed, perhaps the greatest motivation to discover the mechanism of a mysterious reaction is to uncover key examples of that mysterious reaction in your very own laboratory. The stories of 20 chemists and R. B. Woodward are discussed in this paper which is Paper 6 in a 27‐paper series on the history of Woodward‐Hoffmann rules. Social, political, and scientific explanations will also be presented as partial explanations as to why none of these individuals – except Woodward with Hoffmann – solved the pericyclic no‐mechanism problem.

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“…[164][165][166][167][168][169][170] It is, however, clear that the C 1 -C 6 s-bond must to some degree interact with the empty p orbital at C 11 and that "homoconjugation" between them becomes the important factor in stabilizing such a "bent" cyclopropyl species. Thus, it must be considered as a bent cyclopropyl cation.…”

Section: ð3:30þmentioning

confidence: 99%