Ring expansion of geminal dibromocyclopropanes with silver fluoride : a convenient route to fluorinated medium-sized rings

H.J.J. Loozen, W.M.M. Robben, H.M. Buck

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

5 Citaten (Scopus)

Samenvatting

Ring opening of the geminal dibromocyclopropanes 1-3 can be effected by treatment with silver fluoride in acetonitrile. In a stereospecific reaction this affords the allylic fluorides 4-8 in moderate yields. This reaction follows the general principles which have been established for silver ion-catalyzed ring expansions in medium sized rings. Treatment of 7-exo-bromo-7-endo-iodobicyclo[4.1.0]heptane (10) with AgF affords 2-bromo-3-fluoro-1-cycloheptene (11). On using AgPF6 as a catalyst in the ring opening of 10, a Ritter reaction is observed giving N-(2-bromo-1-cycloheptene-3-yl)acetamide (12).
Originele taal-2Engels
Pagina's (van-tot)248-249
TijdschriftRecueil des Travaux Chimiques des Pays-Bas
Volume95
Nummer van het tijdschrift10
DOI's
StatusGepubliceerd - 1976

Vingerafdruk

Duik in de onderzoeksthema's van 'Ring expansion of geminal dibromocyclopropanes with silver fluoride : a convenient route to fluorinated medium-sized rings'. Samen vormen ze een unieke vingerafdruk.

Citeer dit