Reference

Synthesis of mono- and difunctional oligoisobutylenes - III

Synthesis of mono- and difunctional oligoisobutylenes - III. Modification of a-chlorooligoisobutylene by reaction with maleic anhydride. Tessier, M.; Marechal, E. (Lab. Synth. Macromol., Paris 75005, Fr.). Eur. Polym. J., 20(3), 269-80 (English) 1984. CODEN: EUPJAG. 1122-17-4 and 9003-27-4 which are cas registry numbers are also used here. ISSN: 0014-3057. DOCUMENT TYPE: Journal CA Section: 35 (Chemistry of Synthetic High Polymers) Section cross-reference(s): 27 A preliminary study of the thermal dehydrochlorination of a-chlorooligoisobutylene indicated that the double bond of the resulting olefin could be endo (i.e., providing Me2C:CH end groups) or exo (i.e., providing CH2:CMeCH2 end groups). Ene reaction of maleic anhydride (I) with this oligomer was studied on a model, 2,4,4-trimethyl-1-pentene [107-39-1]; the resulting mixt. was completely analyzed by 13C- and 1H-NMR spectroscopy, indicating formation of 2 isomeric oligomer anhydrides. Ene synthesis on a-(2-methyl-2-propenyl)oligoisobutylene showed that only exo bonds were able to react and that the functionality of the resulting oligomeric anhydride mixt. was 0.92. In the presence of dichloromaleic anhydride [1122-17-4] catalysts, disubstitution occurred, because the double bond formed in the 1st reaction was able to react a 2nd time with I. .

The activation of compounds with labile chlorine by electrophilic double bonds

The activation of compounds with labile chlorine by electrophilic double bonds. Application to the mechanism of the reaction between chlorinated polyisobutene and maleic anhydride. Weill, J. (Inst. Francais Pet., Lyon-1 Univ., Rueil-Malmaison, Fr.). Report, IFP-30-196; Order No. DE83751063, 316 pp. Avail. NTIS (U.S. 108-31-6 and 9003-27-4 which are cas registry numbers are also used here. Sales Only) From: Energy Res. Abstr. 1983, 8(21), Abstr. No. 50641 (French) 1982. DOCUMENT TYPE: Report CA Section: 35 (Chemistry of Synthetic High Polymers) A structural study of polyisobutylene (I) and chlorinated I and an allylic chlorination method are described. The reactivity of allyl chloride derivs. bearing allylic H atoms with electrophilic double bonds (ene reaction) is discussed. There is evidence for interaction of electrophilic double bonds with labile Cl, resulting in dehydrochlorination. This effect, which explains the mechanism of the industrial reaction of chlorinated I with maleic anhydride, is used in catalysis and explained by theor. calcns. .