Trans-1,3,9-decatriene

CO Me group increases trans selectivity by only 0.1 kcal mol in the decatriene series (compare entries 1-3, Table 2) versus ca. 1.3 kcal mol with the nonatrienes, the additional increases in selectivity due to the COMe and CHO activating groups are comparable in the two series 0.6-0.7 kcal mol for COMe and 0.3-0.4 kcal mol for CHO. ... 

Hgure 28 defines the sterically preferred orientatitm of substiments in the trans- (104) and defused (105) transition states for conformationally mobile mmiosubstituted 1,7,9-decatrienes. Substituents at R and R will preferentially occupy the sterically less demanding equatorial positions in both transition states. Dienylic R substituents generally adopt an equatorial position in the tran.r-fused transitimi state (104), while an axial orientation appears to be sterically favored in the cis transition state (105) (for example, refer to cyclizations of (17) and (18), Figure 6). Equatorial placement of R in (105) introduces... 

The stoichiometry of the crystalline complex obtained by reaction of cyclic oligoolefins with AuCl in absolute ether at room temperature (0°C for norbornadiene) depends upon the olefin. 1,5-Cyclooctadiene and both cis,cis,trans- and oif-infrared spectra of the trienes indicate the presence of both complexed and free double bonds, the cis,cis,trans-l,5,9-cyc odo-decatriene showing one free cis unsaturation. C is,cyclodeca-diene and dicyclopentadieneform, on the other hand, only 1 1 complexes. The former olefin is complexed only at the trans double bond, whereas the latter is complexed only at the double bond in the norbomene part of the molecule (225). 

C12H17NO 2-cis-hydroxymethyl-4-trans-phenyl-1-cyclohe. .. 551.15 48.820 2 24454 C12H180 5,7-di methyl-3,5,9-decatrien-2-one 111317-19-2 524.28 46.221 2... 

Meijboom and Stroink (76) found that 2-trans, A-cis, 7-c/i-decatrienal was the compound responsible for the fishy off-flavors occurring in autoxidized oil containing 0)-3 fatty acids. This trienal was also found in autoxidized methyl DHA by Noble and Nawar (75) and in autoxidized mackerel oil by Ke et al. (77). 

Nitro-substituted trienes have been demonstrated to be highly reactive IMDA reaction substrates14. ( , ..E )-l-Nitro-l,6,8-decatriene cyclized to give predominantly the trans-fused hexahydro-1 /f-indene. 

The conjugated trienes cis. trims,cis-1,3,5-cyclodccalriene (16) and cisjrans,3,5-cycloun-decatriene (17) thermally isomerize with stereospecific formation of the tricyclic alkenes trans-tricyclo[5.3.0.04,6]dec-2-ene (18) and rrany-tricyelo[5.4.0.04-6]undec-2-ene (19) by reactions involving [1,5] sigmalropic hydrogen shifts followed by intramolecular [4 + 2] cycloadditions98. 

Moreover, the starting compound, commercial 1,5,9-decatriene, is a mixture of cis- and trans-isomers, and this theoretically may double the number of diastereomers formed. 

Other carbonyls cis-4-heptenal, trans,cw-2,6-nonadienal, 2,5-octadienal, 2,4,6-nonatrienal, 2,4,7-decatrienal, l-penten-3-one, l-octen-3-one,tra/ts,cw-3,5-octadien-3-one,3,5-undecadien-3-one, 1-octen-... 

Meijboom, P.W. and Stroink, J.B.A. (1972) 2-trans,4-cis,7-cis-decatrienal, the fishy off-flavour occurring in strongly autoxidized oils containing linolenic acid or o)3,6,9, etc., fatty acids. JAOCS 49, 555-558. 

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