Wagner-meerwein rearrangement of the homocubylcarbinyl system, and x-ray structure of 1-bromo-4,4-diphenyl-5-methoxypentacyclo- [5.3.0.02.6.03.9.05.8]decan-10-one ethylene ketal

Mak, Thomas C. W.; Yip, Yu Chi; Luh, Tien‐Yau

doi:10.1016/s0040-4020(01)87614-6

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Introduction1

Preparation Of Strained Cage Alcohols and Their Derivatives1

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1986

2010

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Cited by 8 publications

(2 citation statements)

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“…Thus, reaction of cubane (33) with a stoichiometric amount of [Rh(CO)2Cl]2 affords homocubanone (34). A stable acylrhodium intermediate, 35, has been isolated in this reaction (Scheme 5). 20 Substituted homocubanes have been synthesized via carbene-mediated ring expansions performed in appropriately substituted cubanes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Marchand¹

1989

Chem. Rev.

145

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Section: Introductionmentioning

confidence: 99%

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Marchand¹

1989

Chem. Rev.

145

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“…By careful selection of reagents and reaction conditions, good yields of the corresponding bridgehead alcohols could be obtained. 18,48 In some cases the formation of the alcohols is accompanied by the corresponding bridgehead halogen compounds.18,48 Unexpectedly, diphenylcarbinol 51 behaves differently. Upon treatment with either aqueous HC1 or SOCl2, no bridgehead bishomocubyl alcohol is formed, but instead a high-melting solid is obtained to which no structure has been assigned yet.…”

Section: Preparation Of Strained Cage Alcohols and Their Derivativesmentioning

confidence: 99%

Strained bridgehead cage alcohols and derivatives

Klunder¹,

Zwanenburg²

1989

Chem. Rev.

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Wagner‐Meerwein Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The class of 1,2‐rearrangement of carbocation intermediates, from which the migratory group rearranges from an adjacent carbon atom to the carbocation center to form a more stable carbocation or to alleviate the ring strain, is generally known as the Wagner–Meerwein rearrangement. The Wagner–Meerwein rearrangement is generally observed in fused cyclic compounds, such as bicyclic terpene systems. In general, this rearrangement can be initiated under different conditions, which promote the generation of carbocation intermediates. However, due to the carbocationic nature of the rearrangement, this rearrangement sometimes leads to a complicated mixture of products. The modifications for this reaction include the photolysis, thermolysis of azo ‐compounds, and radical initiation of epoxide by Cp 2 TiCl and azo ‐compound by triphenyl pyrylium tetrafluoroborate. This reaction has been broadly applied in organic synthesis.

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Wagner-meerwein rearrangement of the homocubylcarbinyl system, and x-ray structure of 1-bromo-4,4-diphenyl-5-methoxypentacyclo- [5.3.0.02.6.03.9.05.8]decan-10-one ethylene ketal

Cited by 8 publications

References 13 publications

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Strained bridgehead cage alcohols and derivatives

Wagner‐Meerwein Rearrangement

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