242. Union of aryl nuclei. Part V. A modification of the Gomberg reaction

The orienting influence of the methyl group in toluene in the gomberg reaction

“…Sodium acetate (900 g.) was added, and the mixture stirred for 20 hours, during which time the temperature rose to 27' (cf. Elks, Haworth & Hey, 1940). After removal of excess toluene from the toluene layer, the residual oil was distilled under reduced pressure and the fraction boiling at 170-220'/15 mm.…”

Free‐radical 4‐nitrophenylation of thieno[2,3‐b]pyridine. Part 3: Consideration of mechanistic and selectivity factors involved in the substitution process

“…In this modified Gomberg-Bachmann-Hey reaction [3][4][5][6] diazo compound 2 is assumed to undergo thermal dissociation to yield the 4-nitrophenyl free radical (4) [7] which attacks a CH carbon atom, e.g. C3 of 1, directly to give a resonance-stabilized free radical 5 [8], from which an adventitious free radical (usually acetoxy, as shown) abstracts a hydrogen atom to give 3b (See Scheme 1).…”

Quantitative Investigation of Homolytic Arylation

“…References: ^omberg (1900); 2 Hodgson and Marsden (1940); 3 Grieve and Hey (1934); 4 Elks and Hey (1943); 5 Grieve and Hey (1932); 6 Case (1938); 7 France, Heilbron and Hey (1938); 8 Elks, Haworth and Hey (1940); 9 Hey and Lawton (1940); 10 Hey (1934); n Butterworth, Heilbron, Hey and Wilkinson (1938); 12 Heilbron, Hey and Wilkinson (1938); 13 Gomberg and Pernert (1926); 14 Möhlau and Berger (1893b); 15 Wieland, Popper and Seefried (1922); ie Bamberger (1895); 17 Bamberger (1896); 18 Franc^ Heilbron and Hey (1939); 19 Kliegl and Huber (1920); 20 Kuhling (1895Kuhling ( , 1896; 21 Dietrich (1925); 22 Lippmann (1886); 23 Hey (1932); 24 Dunstan and Hughes (1946); 25 Harley-Mason and Mann (1940); 26 Gomberg and Bachmann (1924); 27 Hey and Walker (1948); 28 Haworth, Heilbron and Hey (1940a); 29 Haworth, Heilbron and Hey (1940b); 30 Wieland and co-workers (1930Wieland and co-workers ( , 1934...…”