(4E,6E)-2,6-dimethylocta-2,4,6-triene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The following examples show that conjugated diene units can also be incorporated in butyl elastomers by carbocationic copolymerization with isobutylene. Technical grade (80%) alloocimene, (2,6-dimethyl-2,4,6-octatriene) of 95.6% actual purity level which was purchased from Aldrich and dried by column chromatography using aluminum oxide (neutral, Brockmann I activity (Aldrich) and degassed by freeze-pump-thaw technique. Isobutylene (IB), 99% purity and methyl chloride (MeCl), 99.5% purity (Matheson TRIGAS) were condensed from gas phase after drying it by passing through a column filled with BaO/CaCl2. Hexane(s) (Mallinckrodt Chemicals with 98.5% minimum purity) was freshly distilled off CaH2 (Aldrich). Di-tert-butylpyridine (DtBP, 97%, TIC), N,N-Dimethyl acetamide (DMA, 99.8%, anhydrous, Aldrich) and titanium tetrachloride (TiCl4, 99.9%, Aldrich) were used as received. p-Vinylcumyl methyl ether (inimer) was synthesized based on the procedure described in (C. Paulo, J. E. Puskas, Macromolecules 2001, 34, 734-739). It was purified by column chromatography using neutral Brockmann activity I alumina (Aldrich) and n-pentane. 2-Chloro-2,4,4-trimethylpentane (TMPCl) was made by hydrochlorination of 2,4,4-trimethylpent-1-ene (TMP-1, Acros). After completion of the reaction, solution was neutralized by the slow addition of sodium bicarbonate, dried over CaH2 and filtered. It was degassed with freeze-pump-thaw cycles. dried by column chromatography degassed by freeze-pump-thaw technique condensed from gas phase after drying it filled with BaO/CaCl2 Hexane(s) (Mallinckrodt Chemicals with 98.5% minimum purity) was freshly distilled off CaH2 (Aldrich) It was purified by column chromatography After completion of the reaction, solution dried over CaH2 filtered It was degassed with freeze-pump-thaw cycles

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 408 g of allo-ocimene (85% 4E 6Z, 15% 4E 6E) and 202 g of acrolein were placed in a stainless steel vessel which is equipped to withstand a high internal pressure at elevated temperatures. 1 gm of hydroquinone, a polymerisation inhibitor, was added. The air in the vessel was displaced with nitrogen and the vessel closed. The temperature was raised to 145°-150° C. and maintained in the range for 7.5 hours. The maximum pressure recorded was 105 psi. The reaction mixture was then distilled and a mixture of four aldehydes collected which represented a 66% yield of the desired product. The percentages of adducts were A 4%, B 11%, C 74% and D 11% where the letters A, B, C, D represent the isomers denoted as such in Example 1. which is equipped the vessel closed The temperature was raised to 145°-150° C. maintained in the range for 7.5 hours The reaction mixture was then distilled a mixture of four aldehydes collected which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 554 g of allo-ocimene (85% 4E, 6Z; 15% 4E, 6E) and 224 g of acrolein were placed in a stainless steel vessel which is equipped to withstand a high internal pressure at elevated temperatures. 1 gm of embanox, a polymerisation inhibitor, was added. The air in the vessel was displaced with nitrogen and the vessel was closed. The temperature was raised to 165°-170° C. and maintained in the range for 6 hours. The maximum pressure recorded was 150 psi. The reaction mixture was then distilled and a mixture of four isomeric aldehydes collected which represented a 70% yield of the desired product. The percentages of adducts were determined by GLC to be as follows: ##STR6## which is equipped the vessel was closed The temperature was raised to 165°-170° C. maintained in the range for 6 hours The reaction mixture was then distilled a mixture of four isomeric aldehydes collected which

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Maleic anhydride (39.88 g), 0.407 mol) and allo-ocimene (55.34 g, 0.407 mol) were charged in a 250 ml three necked round-bottom flask, connected with a reflux condenser. Immediately after addition of the maleic anhydride to the allo-ocimene, the mixture turned intense orange/yellow. The mixture was warmed carefully to 50° C. Then, as the maleic anhydride started to melt, a violent and exothermic Diels-Alder reaction took place. The temperature rose rapidly to 170-190° C. while the color of the mixture became less intense. After about 10 minutes the temperature started to drop. The mixture was kept at 100° C. for one hour. 93.71 g (0.401 mol=98.4%) of a yellow product was obtained that solidified on standing (melting point 78-82° C.). The product was washed with pentane in order to remove the yellow color to a great extent. The yield dropped during washing to about 65%. The anhydride was recrystallized from heptane to yield a white solid (melting point 83.5° C.-84° C.). Yield after recrystallization was 60%). connected with a reflux condenser a violent and exothermic Diels-Alder reaction rose rapidly to 170-190° C. while the color of the mixture The mixture was kept at 100° C. for one hour 93.71 g (0.401 mol=98.4%) of a yellow product was obtained that solidified The product was washed with pentane in order to remove the yellow color to a great extent The yield dropped during washing to about 65% The anhydride was recrystallized from heptane