IPSO-CHLORINATION OF PARA-ALKYLPHENOLS ET HERS WITH SBF5-CH2CL2(CHCL3, CCL4) - A NOVEL ROUTE TO 4-CHLOROCYCLOHEXA-2,5-DIENONES

Authors
JOUANNETAUD MP JACQUESY JC KARAM O COUSTARD JM FERRON B
Citation
Mp. Jouannetaud et al., IPSO-CHLORINATION OF PARA-ALKYLPHENOLS ET HERS WITH SBF5-CH2CL2(CHCL3, CCL4) - A NOVEL ROUTE TO 4-CHLOROCYCLOHEXA-2,5-DIENONES, Bulletin de la Societe chimique de France, 131(3), 1994, pp. 284-290
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
131
Issue
3
Year of publication
1994
Pages
284 - 290
Database
ISI
SICI code
0037-8968(1994)131:3<284:IOPEHW>2.0.ZU;2-#
Abstract
Chlorination of mono or Polycyclic para-alkylphenols ethers with SbF5- CH2Cl2 (CHCl3, CCl4) gives the corresponding 4-chlorocyclohexa-2,5-die nones in a better yield than reaction with SbCl5-CH2Cl2(SO2). The post ulated mechanism implies electrophilic chlorination with chloromethyl cations (ClCH2)2Cl+, CHCl2+ or CCl3+ formed in situ to yield the ionic species, the precursors of the dienones, which have been characterize d by NMR. In the reaction conditions, no alpha-chlorination to a carbo nyl group is observed.