A facile and stereoselective approach to geminal endo-iodo-exo-bromocyclopropanes; application in the synthesis of medium-sized rings

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

doi:10.1002/recl.19760951008

A facile and stereoselective approach to geminal endo-iodo-exo-bromocyclopropanes; application in the synthesis of medium-sized rings

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

Chemical Engineering and Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

3 Citations (Scopus)

Abstract

Geminal dibromocyclopropanes annelated to six-, seven- or eight-membered rings can be converted easily to their geminal endo-lithio-exo-bromo derivatives when treated with butyllithium at -95°. Upon reaction of these derivatives with iodine at -95° the corresponding geminal endo-iodo-exo-bromocyclopropanes are obtained in good yields. The structure assignments are made by means of some silver ion-assisted ring expansions.

Original language	English
Pages (from-to)	245-247
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	95
Issue number	10
DOIs	https://doi.org/10.1002/recl.19760951008
Publication status	Published - 1976

Access to Document

10.1002/recl.19760951008

Cite this

@article{197914390fe840708dbe86be07397649,

title = "A facile and stereoselective approach to geminal endo-iodo-exo-bromocyclopropanes; application in the synthesis of medium-sized rings",

abstract = "Geminal dibromocyclopropanes annelated to six-, seven- or eight-membered rings can be converted easily to their geminal endo-lithio-exo-bromo derivatives when treated with butyllithium at -95°. Upon reaction of these derivatives with iodine at -95° the corresponding geminal endo-iodo-exo-bromocyclopropanes are obtained in good yields. The structure assignments are made by means of some silver ion-assisted ring expansions.",

author = "H.J.J. Loozen and W.M.M. Robben and H.M. Buck",

year = "1976",

doi = "10.1002/recl.19760951008",

language = "English",

volume = "95",

pages = "245--247",

journal = "Recueil des Travaux Chimiques des Pays-Bas",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "10",

}

TY - JOUR

T1 - A facile and stereoselective approach to geminal endo-iodo-exo-bromocyclopropanes; application in the synthesis of medium-sized rings

AU - Loozen, H.J.J.

AU - Robben, W.M.M.

AU - Buck, H.M.

PY - 1976

Y1 - 1976

N2 - Geminal dibromocyclopropanes annelated to six-, seven- or eight-membered rings can be converted easily to their geminal endo-lithio-exo-bromo derivatives when treated with butyllithium at -95°. Upon reaction of these derivatives with iodine at -95° the corresponding geminal endo-iodo-exo-bromocyclopropanes are obtained in good yields. The structure assignments are made by means of some silver ion-assisted ring expansions.

AB - Geminal dibromocyclopropanes annelated to six-, seven- or eight-membered rings can be converted easily to their geminal endo-lithio-exo-bromo derivatives when treated with butyllithium at -95°. Upon reaction of these derivatives with iodine at -95° the corresponding geminal endo-iodo-exo-bromocyclopropanes are obtained in good yields. The structure assignments are made by means of some silver ion-assisted ring expansions.

U2 - 10.1002/recl.19760951008

DO - 10.1002/recl.19760951008

M3 - Article

SN - 0165-0513

VL - 95

SP - 245

EP - 247

JO - Recueil des Travaux Chimiques des Pays-Bas

JF - Recueil des Travaux Chimiques des Pays-Bas

IS - 10

ER -

A facile and stereoselective approach to geminal endo-iodo-exo-bromocyclopropanes; application in the synthesis of medium-sized rings

Abstract

Access to Document

Fingerprint

Cite this