Steric and electronic factors in the addition of phenylsulfinyl carbene to methyl-substituted ethylenes.

Venier, Clifford G.; Ward, Mark A.

doi:10.1016/s0040-4039(01)85597-0

Cited by 5 publications

(1 citation statement)

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“…The stability has been attributed to a powerful electrondonating ability of the PhS(0) substituent under conditions of high electron demand. 59 Small amounts of asymmetric induction are observed in the cuprous chloridecatalysed additions of chiral carboalkoxycarbenes to olefins6' Substituted methylenecyclopropanes are formed by the addition of carboethoxycarbene to 1,ldimethylallene.61…”

Section: S a M A T Hmentioning

confidence: 99%

Chapter 5. Arynes, carbenes, nitrenes, and related species

Matlin¹

1978

Annu. Rep. Prog. Chem., Sect. B

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The use of complex bases for the generation of arynes has been reviewed by Caubkre.' Diels-Alder reactions of benzyne with 1-vinylcyclobutene or with 1,2-dimethylenecyclobutane lead to tricyclic adducts (Scheme 1) which can be dehydrogenated with DDQ to give naphtho[a]cyclobutene or naphtho[b]cyclobutene, respectively. Similar reactions of 2,3-didehydronaphthalene with the dienes provide synthetic routes to anthrocyclobutenes.' Scheme 1 Arynic condensations have been used in several new syntheses of heterocyclic systems. Condensation of benzyne with diazocyclopentadienes gives 3H-indazole-(3-~piro)-cyclopentadienes.~ Treatment of N-phenyl 2-chlorobenzylamines or of N-phenyl 3-bromobenzylamines with potassium amide in liquid ammonia affords mixtures of dihydrophenanthridines and dihydrobenzazetes (Scheme 2).4 R 1 Ra/ \ Scheme 2

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Section: S a M A T Hmentioning

confidence: 99%