An Improved Synthesis of Cyclopropa[4,5]benzocyclobutene (Rocketene)

McNichols, Aileen T.; Stang, Peter J.

doi:10.1055/s-1992-21549

Cited by 18 publications

(12 citation statements)

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“…Pale yellow microcrystals (95 mg, 39%) from flash chromatography (ethyl acetate-light petroleum, 3 : 1 ; and crystallisation from the same solvent); mp 182.5-183. 5 (29), 175 (12) and 150 (14); p(C6H6, 21 "C)/D 3.37.…”

Section: -(4'-pyridylmethylidene)-lh-~yclopropa[ B] Naphthalene 12kmentioning

confidence: 99%

Studies in the cycloproparene series; heterocyclic substituted methylidenecyclopropa[b]naphthalenes

Halton¹,

Cooney²,

Davey³

et al. 1995

J. Chem. Soc., Perkin Trans. 1

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Section: -(4'-pyridylmethylidene)-lh-~yclopropa[ B] Naphthalene 12kmentioning

confidence: 99%

Studies in the cycloproparene series; heterocyclic substituted methylidenecyclopropa[b]naphthalenes

Halton¹,

Cooney²,

Davey³

et al. 1995

J. Chem. Soc., Perkin Trans. 1

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“…57 Recently, this methodology has been used for the improved preparation of cyclopropa[4.5]benzocyclobutene 67 (rocketene) (Scheme 37). 58…”

Section: [21212] Cycloaddition Approachesmentioning

confidence: 99%

Recent chemistry of benzocyclobutenes

2001

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“…However, the authors employed −OMe as the benzylic leaving group with the result that the ring closure proceeded in 5% yield only. As −OSiMe 3 is a better leaving group in electrophilic aromatic substitution reactions than −OMe, McNichols and Stang found that its use here also improved the overall yield of 5 to 32% some 10 years ago as illustrated in Scheme . Thus, cobalt-catalyzed co-oligomerization of hexa-1,5-diyne with 1-tributylstannyl-3-trimethylsilyloxypropyne 9 paralleled the Saward and Vollhardt reaction efficiency and gave the ortho - difunctionalized cyclobutabenzene 10 in 50% yield.…”

mentioning

confidence: 93%