Cationic Carbenoid Rearrangement of 2‐Phenyl Substituted <i>gem</i>‐Dihalogenospiropentanes

Sedenkova, Kseniya N.; Averina, Elena B.; Grishin, Yuri K.; Rybakov, Victor B.; Kuznetzova, Tamara S.; Зефиров, Н. С.

doi:10.1002/ejoc.201000427

Cited by 8 publications

(4 citation statements)

References 23 publications

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“…Bromofluorospiropentane on treatment with MeLi gave a tricyclic system exclusively (Scheme 58). 24 At the same time the reaction between MeLi and bromochlorospiropentane gave exclusively the hexacyclic dimeric product. If the dibromo compound was subjected to the reaction, a mixture of tricyclic and dimerized products was obtained.…”

Section: Rearrangementsmentioning

confidence: 99%

“…Sometimes the dihalocyclopropane derivatives are essential as reactive intermediates for the synthesis of naturally occurring compounds. 24 Here, dibenzo-18-crown-6 was used as the phase transfer catalyst for the generation of bromofluorospiropentane, TEBAC for bromochlorocyclopropane and KO t Bu for dibromocyclopropane derivatives, respectively. In the preparation of (±) grenadamide, use of dibromocarbene for cyclopropanation under phase transfer catalysis was employed (Scheme 12).…”

Section: Phase Transfer Catalysis In the Synthesis Of Gem-dihalocyclomentioning

confidence: 99%

“…23 The synthesis of dihalospiropentanes 36 by the cyclopropanation of alkylidenecyclopropanes 35 under phase transfer conditions is reported (Scheme 14). 24 Here, dibenzo-18-crown-6 was used as the phase transfer catalyst for the generation of bromofluorospiropentane, TEBAC for bromochlorocyclopropane and KO t Bu for dibromocyclopropane derivatives, respectively.…”

Section: Phase Transfer Catalysis In the Synthesis Of Gem-dihalocyclo...mentioning

confidence: 99%

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Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

et al. 2015

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gem-Dihalocyclopropanes have wide-spread applications in organic synthesis due to their versatile chemistry. They can serve as substrates for a large range of useful materials such as natural products, alkaloids, cyclopropanes, heterocycles, aromatic ring systems etc. Normally the dihalocyclopropanes are prepared by the addition of dihalocarbene to alkene, but due to the great synthetic efficacy of gem-dihalocyclopropanes a number of methods have been developed for their synthesis. Generally gem-dihalocyclopropanes exist as strained cyclic systems with astonishing kinetic stability. They are capable of undergoing transformations leading to a variety of products which have potential applications in various synthetic organic chemistry fields.

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Section: Rearrangementsmentioning

confidence: 99%

Section: Phase Transfer Catalysis In the Synthesis Of Gem-dihalocyclomentioning

confidence: 99%

Section: Phase Transfer Catalysis In the Synthesis Of Gem-dihalocyclo...mentioning

confidence: 99%

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Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

et al. 2015

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“…By analogy to the synthesis of dichlorocyclopropanes, Averina et al reported the addition of bromofluorocarbene to olefins to synthesize gem-bromofluorocyclopropanes. 12 In their early report, the authors reported the use of a bi-…”

Section: Addition Of Fluorocarbenes To Alkenesmentioning

confidence: 99%

Synthesis and Applications of Fluorocyclopropanes

et al. 2016

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The combination of a fluorine atom and a cyclopropane ring, which both possess unique structural and chemical features, can generate new relevant scaffolds with potential interest for the synthesis of new bioactive compounds. In this review, we report the impressive progress recently devoted to the synthesis of fluorocyclopropanes especially using asymmetric methods and highlight some recent reported applications. 1 Introduction 2 Addition of Carbenes to Fluoroalkenes 3 Addition of Fluorocarbenes to Alkenes 4 Michael Initiated Ring Closure 5 Nucleophilic Fluorination 6 Applications to the Synthesis of Biorelevant Compounds 7 Conclusion

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Benzylidenecyclopropane

Zhang¹,

Shi²

2013

Encyclopedia of Reagents for Organic Synthesis

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Cationic Carbenoid Rearrangement of 2‐Phenyl Substituted gem‐Dihalogenospiropentanes

Abstract: The series of 2-phenyl-and 2,2-diphenyl gem-dihalogenospiropentanes were employed as model compounds to study the carbenoid rearrangement with the use of methyllithium.

Cited by 8 publications

References 23 publications

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

Synthesis and Applications of Fluorocyclopropanes

Benzylidenecyclopropane

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