Friedel-Crafts and Related Chemistry

3 SbXs-Catalyzed Reactions 11.3.1 Friedel-Crafts and Related Chemistry 

Aromatic compounds can be readily alkylated under SbCls catalysis [10,11], although competing chlorination can sometimes complicate the alkylation. The acidity of SbCls is comparable with that of AICI3 and AlBrs in the reaction of s-butyl chloride with benzene [10a]. 

Much of the research on the SbCls-catalyzed halogenation of arenes has focused on the chlorination and bromination of perfluoroalkyl-substituted aromatics [14]. The reaction of organic disulfides with electron-rich aromatic compounds under catalysis with SbCls and AgSbFg affords unsymmetrical aryl sulfides in modest yields [15a]. Electrophilic sulfinylation and sulfonation can be similarly effected by SbCls [15a-c]. Alkyl- and halobenzenes give thiocyano derivatives when treated with a mixture of SbCls and Pb(SCN)2 in CCI4 [16], 

Silyl enolates of a,a-dialkoxy ketones react with furans to form [3 4- 4] cycloaddition products in the presence of SbCls (Eq. 6) [17], Cycloaddition also occurs when 2,2-dialkoxycyclopropanecarboxylic esters and carbonyl compounds are treated with SbCls [18]. 

In the presence of SbCls and Sn(OTf)2, a,/l-unsaturated thioesters react with silyl enol ethers to form the corresponding Michael adducts stereoselectively in high yields [19]. Successive treatment of lactones with ketene silyl acetals and certain orga-nosilane-based nucleophiles under SbCls-McsSiCl-Snla catalysis affords a-amino- or a,a-disubstituted cyclic ethers (Eq. 7) [20], 

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Reactions.—Electrophilic Attack by Phosphorus. This year has seen a resurgence in Friedel-Crafts and related chemistry of the halogenophosphines, with the general objective of establishing mechanisms. For example, the conversion of phosphorus trichloride into complexes of either dichlorophenylphosphine (28) or chlorodiphenylphosphine (29) has been studied in order to establish the... 

Friedel-Crafts and Related Reactions, Vols. I-IV (ed), 1963-1964. Carbonium Ions (ed. with Schleyer), Vols. I-V, 1968-1972. Friedel-Crafts Chemistry, 1973. 

For a monograph, see Roberts, R.M. Khalaf, A.A. Friedel-Crafts Alkylation Chemistry Marcel Dekker NY, 1984. For a treatise on Friedel-Crafts reactions in general, see Olah, G.A. Friedel-Crafts and Related Reactions Wiley NY, 1963-1965. Volume 1 covers general aspects, such as catalyst activity, intermediate complexes, and so on. Volume 2 covers alkylation and related reactions. In this volume the various reagents are treated by the indicated authors as follows alkenes and alkanes, Patinkin, S.H. Friedman, B.S. p. 1 ... 

G. A. Olah, ed., Friedel-Crafts and Related Reactions, Vols. 1-1V, Wiley-Interscience, New York, 1962-1964. R. M. Roberts and A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York, 1984. 

For reviews, see Groves Chem. Soc. Rev. 1972, 1. 73-97 Satchcll Satchell in Patai The Chemistry of the Carbonyl Group, vol. 1 Wiley New York, 1966, pp. 259-266. 270-273 Nenitzescu Balaban. in Olah Friedel-Crafts and Related Reactions, vol. 3 Wiley New York, 1964, pp. 1033-1152. 

Olah G. A. in Friedel-Crafts and related reactions , Wiley-Interscience, Vol. I-IV, New York (1963-1964) Olah G. A. in Friedel-Crafts Chemistry , Wiley-Interscience, New York (1973). 

From 1963 to 1965 Professor George Andrew Olah (Nobel Prize in Chemistry in 1994 Figure 1.3) edited and, in part, wrote a comprehensive treatise entitled Friedel-Crafts and Related Reactions. This monograph was published in four volumes covering more than 5,000 pages (with about... 

Pharmaceutical Chemistry, Drug Synthesis Roth, H. J. Kleemann, A. T. Beisswenger, T., Eds. John Wiley New York, New York, 1987 Vol.l. Friedel-Crafts and Related Reactions Olah, G. A., Ed. John. Wiley New York, New York, 1964 pp 1-382. 

Reviews P. E. Spoerri, A. S. DuBois, Org. React. 5, 387 (1949) Thomas, Anhydrous Aluminum Chloride in Organic Chemistry (New York, 1941) p 504 W. Ruske in Friedel-Crafts and Related Reactions vol. Ill, Part 1, G. A. Olah, Ed. (Interscience, New York, 1964) p 383 M. I. Amer et al, J. Chem. Soc. Perkin Trans. 11983,1075 V. V. Arkhipov etal, Chem. Heterocycl. Compd. 33, 515 (1997) R. Kawecki et ah, Synthesis 1999,751. Cf. Gatterman Aldehyde Synthesis Houben-Fischer Synthesis. 

Friedel-Crafts and Grignard processes applied to, 6, 251-289 halogen oxidation of simple, 3, 129-184 infrared spectra of, 12, 13-33 mechanisms of replacement reactions in chemistry of, 9, 1-57 metabolism of, 2, 119-160 3, 229-250 orthoesters of, 1, 77-127 periodate oxidation of, 11, 1-41 the dialdehydes" from, 16, 105-158 physicochemical properties of, 16,11-51 radiation chemistry of, 16, 13-58 and related compounds, paper chromatography of, 9, 303-353 relative reactivities of hydroxyl groups of, 8, 1-44... 

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