Enyne–Allenes

Wang, Kung K.

doi:10.1002/9783527619573.ch20

Cited by 10 publications

(1 citation statement)

References 82 publications

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“…Presumably, the cascade sequence involved an initial 1,3-protropic rearrangement to form the corresponding benzannulated enyne–allene 10a . A Schmittel cyclization reaction [ 1 – 4 ] generates biradical 11a, which then undergoes an intramolecular radical–radical coupling to afford 12a . This is followed by a second prototropic rearrangement to restore the aromaticity to furnish 13a as proposed previously [ 5 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Wang¹,

Bailey²,

Petersen³

et al. 2011

Beilstein J. Org. Chem.

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Summary5-(2-Methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene were synthesized by treatment of the corresponding benzannulated enediynes with potassium tert-butoxide in refluxing toluene to give benzannulated enyne–allenes for the subsequent Schmittel cascade cyclization reactions. The structures of these two 5-(1-naphthyl)-11H-benzo[b]fluorenes could be regarded as 2,2'-disubstituted 1,1'-binaphthyls with the newly constructed benzofluorenyl group serving as a naphthyl moiety.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Wang¹,

Bailey²,

Petersen³

et al. 2011

Beilstein J. Org. Chem.

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Schmittel Cyclization

2010

Comprehensive Organic Name Reactions and Reagents

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The Schmittel cyclization is an intramolecular C 2 ‐C 6 cyclization of hepta‐1,2,4‐triene‐6‐yne (i.e., enyneallene) to form a five‐membered cyclic structure via a methyl fulvene biradical intermediate. It has been reported theoretically that the Schmittel cyclization is disfavored by 25 Kcal/mol with respect to the Myers–Saito cyclization. Furthermore, several features of the Schmittel cyclization have been compared with the Myers–Saito cyclization. The study finds that benzannulation and oxyanion of enyne‐allenes facilitate the Schmittel cyclization.

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Synthesis of Bowl‐Shaped and Basket‐Shaped Fullerene Fragments Via Benzannulated Enyne‐Allenes

Wang

Cui

2011

Fragments of Fullerenes and Carbon Nanotubes

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Enyne–Allenes

Cited by 10 publications

References 82 publications

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Schmittel Cyclization

Synthesis of Bowl‐Shaped and Basket‐Shaped Fullerene Fragments Via Benzannulated Enyne‐Allenes

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