A Novel Synthesis of Branched High-molecular-weight (C_<40>^+) Long-chain Alkanes(Organic Chemistry)

概要

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Many biological and geochemical questions remain concerning the structures, functions, and properties of naturally occurring high-molecular-weight (C_<40>^+ alkanes with various mid-chain alkylation patterns. Above C_<40>, these alkanes are exceedingly difficult to separate and purify, and syntheses can be blocked by the low solubility of intermediates. To overcome these problems, a facile three-step synthesis employing the alkylation of 1,3-dithiane with a suitable α, ω-dibromoalkane was developed. Bisalkylation of the bis(dithianyl)alkane intermediate with the appropriate 1-bromoalkane and subsequent desulfurization with Raney nickel furnished the desired long-chain alkane. Long-chain alkanes modified at mid-chain and/or symmetrically near the chain termini (or unmodified, i. e., long-chain n-paraffins) are accessible by the selection of appropriate bromoalkanes. Nine mid-chain methylated (C_<38>H_<78> to C_<53>H_<108>), one symmetrical terminal-chain dimethylated (C_<40>H_<82>), and four linear (C_<44>H_<90> to C_<58>H_<118>) long-chain alkanes were synthesized by using this approach. High-temperature gas chromatography (HTGC) was found to have important advantages for evaluating the purity of the synthetic high-molecular-weight alkanes.
社団法人日本農芸化学会の論文
2002-03-23