Untersuchungen über Alloïsomerie

Michael, Arthur

doi:10.1002/prac.18950520123

Cited by 28 publications

(7 citation statements)

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“…(Z)-2,3-DiphenylpropenitriIe (44), mp 86-87 °C (lit.00 88 °C). (E)-2,3-Diphenylpropenitrile (45). This material was prepared by dehydrating the corresponding oxime.…”

mentioning

confidence: 99%

Survey of carbon-13-hydrogen splittings in alkenes

Kingsbury¹,

Draney²,

Sopchik³

et al. 1976

J. Org. Chem.

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“…(Z)-2,3-DiphenylpropenitriIe (44), mp 86-87 °C (lit.00 88 °C). (E)-2,3-Diphenylpropenitrile (45). This material was prepared by dehydrating the corresponding oxime.…”

mentioning

confidence: 99%

Survey of carbon-13-hydrogen splittings in alkenes

Kingsbury¹,

Draney²,

Sopchik³

et al. 1976

J. Org. Chem.

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“…Both of these processes are E1cB reactions. Following this, the transformation 167 → 168 under basic conditions was indeed discovered to be 50 times faster than 169 → 168 [28,29]. Also, cis-dichloroethylene 170 is transformed into chloroacetylene 171 approximately 20 times faster than trans-dichloroethylene 172 [30].…”

Section: Tandem Skeletal Changes and Polyene Cyclizationmentioning

confidence: 99%

Reactions on Saturated and Unsaturated Carbons

Yadav¹

2021

Steric and Stereoelectronic Effects in Organic Chemistry

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This chapter uncovers the geometrical requirements for reactions on saturated and unsaturated carbons in both acyclic and cyclic systems with the related stereochemical features. The nucleophilic attacks in S N 2 and S N 2 processes, involving the necessary geometrical requirements, are discussed. The resonance-driven activation of cyclopropane is of much significance in synthetic chemistry. The mode of activation and its consequences on product profile are amply reasoned. The S N 2-originated 1,2-migration within geometrical constraints of the reactant and neighboring group participation under solvolysis conditions have been explained with emphasis on product distribution. The activation of oxirane by Lewis acid, followed by rearrangement under stereochemical effect, is discussed. Given the suitable geometrical disposition of substituents and functional groups in a given molecule, several 1,2migrations can take place in tandem to generate fascinating skeletons. This chemistry has been described with examples of the construction of several steroidal skeletons. Baldwin rules and the preferred exo-trig over endo-trig cyclization are demonstrated with examples using geometrical analysis. The stereoelectronically controlled addition reactions are also highlighted. Inter-and Intramolecular Reactions on Saturated CarbonsThe concerted bond formation and bond cleavage in S N 2 reactions proceed with full stereoelectronic control. In transition structure 2 for the reaction, both the nucleophile and the leaving group are bonded to the central carbon atom, which has acquired an sp 2 character. One lobe of the p orbital on carbon overlaps with an incoming nucleophile and the other with the leaving group. Since the nucleophile approaches the carbon from the direction opposite to the leaving group, the result is Walden inversion or inversion of configuration. The reaction is, thus, controlled by electronic effects that impose certain geometrical restraints on the TS structure.

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“…His criticisms of van't Hoff's stereochemical theory, for example, were taken seriously -such an extensive, multipart critique could not be so easily dismissed. 8 Michael's cogent arguments helped establish stereochemistry in organic chemistry. He also saw weakness in Wislicenus's theory that additions to unsaturated substances necessarily precede cis.…”

Section: In 1886 (Image Courtesy Of Tufts University Archives)mentioning

confidence: 99%

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Untersuchungen über Alloïsomerie

Cited by 28 publications

References 4 publications

Survey of carbon-13-hydrogen splittings in alkenes

Survey of carbon-13-hydrogen splittings in alkenes

Reactions on Saturated and Unsaturated Carbons

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