Chemical Engineers Calculation and Shortcut Deskbook by Chemical Engineering

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The failure to isolate any products other than kohnkene 43 indicates that the high pressure-mediated cycloadditions between 41 and 38 both proceed with the same treble diastereoselectivities as those observed previously at atmospheric pressure for the reaction between 37 and 38. The use of high pressure not only circumvents the problems of low reactivity associated with the second cycloaddition to the diene units in 41, but it also takes advantage of the negative volumes of activation associated with the attainment of the highly-ordered transition states in the sequence of two Diels-Alder reactions (cf.

The structural characterization of kohnkene 43 was aided by the high molecular symmetry (D2h) of the molecule. The observation of (i) only 7 resonances in the broadband-decoupled 13C NMR spectrum for the 7 types of heterotopic carbon atoms, (ii) separate resonances in the 1H N M R spectrum for the 6 sets of heterotopic hydrogen atoms, and (iii) the lack of any signals for either the olefinic or s-cis-butadiene reactive termini were consistent with a closed macropolycyclic structure. The observation of a molecular ion at m/z 713 for [M + H] + in the positive-ion fast atom bombardment mass spectrum (FABMS) provided further evidence for the structure 43.

I cis-l,4-Dichlorobut-2-ene c'H20 .. CH2CI CJH2C ~" ~ ~ ",,If 56 t BuOK/THF/O°C t BuOK/-I-HF/O°Cl 8 ""tCH2C I 1 5 4 57 58 Scheme 12. The synthetic strategy used to obtain the extended syn- and anti-bisdienes,57 and 58, respectively [21, 132]. As a consequence of the (presumed) planar nature of the bisisobenzofuran intermediate 54, the anti-bisdienophile39 can be used as the starting material. Trapping of 54 with two equivalents of cis-l,4-dichlorobut-2-enein situ affords an equimolar mixture of the syn-and anti-tetrachlorides,55 and 56 respectively.

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