Premium
Acid‐Catalyzed Cyclodimerizations via Vinyl Cations as Intermediates
Author(s) -
Griesbaum K.
Publication year - 1969
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196909331
Subject(s) - cyclobutane , cyclobutene , electrophile , allene , chemistry , hydrogen bromide , adduct , catalysis , hydrogen chloride , vinyl bromide , bromide , electrophilic addition , vinyl chloride , medicinal chemistry , hydrogen , photochemistry , organic chemistry , polymer chemistry , bromine , ring (chemistry) , polymer , copolymer
The electrophilic addition of hydrogen chloride and bromide to allene and of hydrogen bromide to methylacetylene at −70 °C leads not only to the simple Markownikoff adducts but also to cis‐ and trans‐1,3‐dihalo‐1,3‐dimethylcyclobutanes. These cyclodimerizations, which evidently proceed via vinyl cations, have opened up new short routes for the synthesis of cyclobutane‐, cyclobutene‐, and bicyclobutane derivatives starting from substrates that are industrially readily accessible.