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Alkali‐Metal‐Mediated Zincation of Polycyclic Aromatic Hydrocarbons: Synthesis and Structures of Mono‐ and Dizincated Naphthalenes
Author(s) -
Clegg William,
Dale Sophie H.,
Hevia Eva,
Hogg Lorna M.,
Honeyman Gordon W.,
Mulvey Robert E.,
O'Hara Charles T.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602288
Subject(s) - chemistry , naphthalene , deprotonation , reagent , zincate , zinc , alkali metal , metal , combinatorial chemistry , organic chemistry , base (topology) , mathematical analysis , mathematics , ion
Zinc twice : Naphthalene is attacked and doubly deprotonated at the 2,6‐position by a synergic sodium zincate base to generate a centrosymmetric dizincated molecule. The approach of alkali‐metal‐mediated zincation can effect dimetalation as well as monometalation of polycyclic aromatic hydrocarbons, thus providing access to new zincated naphthalenes that are inaccessible directly through mainstream organozinc reagents.