Recherches dynamiques sur la réaction de Friedel et Crafts

The Friedel-Crafts Syntheses.

“…Thus the difficulty in acylating or alkylating is increased in a halogenobenzene (42,43), although the exact order of interference for the halogens is not established definitely. In this connection, it has been shown that for sulfone formation chlorobenzene is more resistant than bromobenzene (308).…”

“…It is to be expected that the sulfonyl chlorides will generally introduce a sulfone group in the Friedel-Crafts acylations. In fact, the reaction is generally applicable to sulfonyl chlorides and to aromatic nuclei which undergo acylation (35,308,312,452,313). < >S02C1 c6h6 -S-0 0…”

“…Although this practice yields ketones effectively, it is not generally a desirable method for alkylation, where a definite product and high yield are the major interests. Not only is benzene used in this way, but other liquid reactants such as toluene and chloroor bromo-benzene may be used (308,160). In some cases a substance like carbon tetrachloride may be used if it is one of the reactants (353).…”

“…Carbon disulfide appears to have a specific action on the Friedel-Crafts syntheses, tending to prevent migration of groups (358). It is generally an excellent solvent for a variety of alkylations (144, 343) or acylations (302,257,308). In some cases, carbon disulfide may influence the reaction markedly and in a few cases actually reduce the yield (278) or control the velocity of reaction (353).…”

REACTIONS OF p-CHLOROBENZENESULFONIC ACID AND DERIVATIVES. THE σP* CONSTANT OF THE N,N-DIMETHYLSULFON-AMIDO GROUP

“…The water and nitric acid then were boiled off by heating the mixture until the temperature reached 220°. Upon chilling, the product separated and was collected on a sintered glass funnel and was purified by recrystallization from concentrated hydrochloric acid; yield 11 g.…”