Long‐Lived Cyclopropylcarbinyl Cations

Oláh, George A.; Reddy, P. P.; Prakash, G. K. Surya

doi:10.1002/9780470682531.pat0040

Cited by 2 publications

(2 citation statements)

References 139 publications

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“…By contrast, it has been shown previously that (+)-2-carene epoxide 2, in which the epoxide is apparently conjugated to the cyclopropane [7][8][9][10][11][12][13], shows heightened reactivity compared to typical epoxides when reacted solvolytically with weak protic acids including water [14] (Scheme 1). Unconjugated (+)-3-carene epoxide 3 does not react in the same manner [14,15].…”

Section: Introductionmentioning

confidence: 92%

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Silverberg

Rabb

Reno

et al. 2014

Heterocyclic Communications

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The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

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Section: Introductionmentioning

confidence: 92%

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Silverberg

Rabb

Reno

et al. 2014

Heterocyclic Communications

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show abstract

“…Based on our going interest in the use of gold to streamline the synthesis of valuable building blocks via multicomponent reactions,[13] we decided to investigate the formation of highly substituted carbocycles using indoles 2 and stabilized cyclopropyl alkynes 1 as potential reaction partners ( Scheme ). Cyclopropyl rings are privileged motifs towards the construction of molecular complexity[14] and in combination with alkynes and gold catalysis can offer access to previously unknown molecular assemblies [15]…”

Section: Introductionmentioning

confidence: 99%