4,8-Nonadienoic acid, 4-methyl

Nonadienoic acid, 4-methyl-, trans, ethyl ester, 53, 116 Nonan-5-ol, 52, 22 D-NORANDROST-5-EN-36-0L-16-CARBOXYLIC ACIDS, 52, 53 Norbornene, with ethyl tri-... 

Nonadienoic acid, 4-methyl, trans, ethyl ester)... 

C-18 JH, ClflHttOj, 7-ethyl 9A3 thyl 3 methytoxiranyt) 3-methyl-2,6-nonadienoic acid methyl ester cis-i0,ll-epoxy- -ethyl-3,II-dimethyl-trans,trans-2,6-tridecadienoic acid methyl cis-10,11 -oxido-3, Il-di methyl-7-ethyltrideca-tra ns, tranS 2,6-dienoate. R = C2HV C-17 JH, C HjjOj, cis-10,11 -epoxy-3,7,11-trimethyb trans,irans.Z,6-tridecadienoic acid methyl ester. R — CHj. 

P.EGIO- AND STEREOSELECTIVE CARBOXYLATION OF ALLYLIC BARIUM REAGENTS (E)-4,8-DI-METHYL-3.7-NONADIENOIC ACID... 

The ester moiety is also much less reactive, and selective condensation is achieved [19] with 27 [26] (Eq. 24.17). Hydrolysis of 28a affords the corresponding (6 )-7-methyl-6,8-nonadienoic acid E Z = 96 4) [19a]. 

Organoboranes undergo transmetallation. 1-Hexenylboronic acid (438) reacts with methyl acrylate via the transmetallation with Pd(OAc)2, giving methyl 2,4-nonadienoate (439)[399], The ( )-alkenylboranes 440, prepared by the hydroboration of terminal alkynes, are converted into the alkylated ( )-alkenes 441 by treatment with an equivalent amount of Pd(OAc)2 and triethylamine[400]. The ( )-octenylborane 442 reacts with CO in MeOH in the... 

Allylic carbonates are most reactive. Their carbonylation proceeds under mild conditions, namely at 50 C under 1-20 atm of CO. Facile exchange of CO2 with CO takes place[239]. The carbonylation of 2,7-octadienyl methyl carbonate (379) in MeOH affords the 3,8-nonadienoate 380 as expected, but carbonylation in AcOH produces the cyclized acid 381 and the bicyclic ketones 382 and 383 by the insertion of the internal alkene into Tr-allylpalladium before CO insertion[240] (see Section 2.11). The alkylidenesuccinate 385 is prepared in good yields by the carbonylation of the allylic carbonate 384 obtained by DABCO-mediated addition of aldehydes to acrylate. The E Z ratios are different depending on the substrates[241]. 

Carbonyiation of butadiene gives two different products depending on the catalytic species. When PdCl is used in ethanol, ethyl 3-pentenoate (91) is obtained[87,88]. Further carbonyiation of 3-pentenoate catalyzed by cobalt carbonyl affords adipate 92[89], 3-Pentenoate is also obtained in the presence of acid. On the other hand, with catalysis by Pd(OAc)2 and Ph3P, methyl 3,8-nonadienoate (93) is obtained by dimerization-carbonylation[90,91]. The presence of chloride ion firmly attached to Pd makes the difference. The reaction is slow, and higher catalytic activity was observed by using Pd(OAc) , (/-Pr) ,P, and maleic anhydride[92]. Carbonyiation of isoprcne with either PdCi or Pd(OAc)2 and Ph,P gives only the 4-methyl-3-pentenoate 94[93]. 

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