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[2 + 2]‐Cycloadditions to Strained Bridgehead Olefins. I. 1, 1‐Dichloro‐2,2‐difluoroethene
Author(s) -
Becker Konrad B.,
Hohermuth Martin K.
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650121
Subject(s) - chemistry , bicyclic molecule , regioselectivity , yield (engineering) , nuclear magnetic resonance spectroscopy , stereochemistry , ene reaction , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
The strained bridgehead olefins bicyclo [3.3.1]non‐1‐ene ( 1 ), bicyclo [4.2.1] non‐‐1‐(8) ( 2 ), and bicyclo [4.2.1]non‐1‐ene ( 3 ) react rapidly with 1,1‐dichloro‐2, 2‐‐difluoroethene ( 5 ) to yield mixtures of regioisomeric dichlorodifluorocyclobutanes 8/9, 10/11 and 12/13 , respectively. On the contrary, the reaction of 5 with the model compound ( E )‐l‐methylcyclooctene ( 4 ) is completely regioselective. The structure of the cycloadducts has been elucidated mainly by 19 F‐NMR. and 13 C‐NMR. spectroscopy.