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The preparation of three new partially deuterated hexadecanethiols for applications in surface chemistry

✍ Scribed by Erin E. Sheepwash; Paul A. Rowntree; Adrian L. Schwan

Publisher
John Wiley and Sons
Year
2008
Tongue
French
Weight
191 KB
Volume
51
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of three partially deuterated hexadecanethiols has been achieved. Thiols CH 3 (CH 2 ) 7 (CD 2 ) 8 SH, CD 3 (CD 2 ) 7 (CH 2 ) 8 SH and CD 3 (CH 2 ) 15 SH were targeted, as these compounds, after formation of self-assembled monolayers on Au(1 1 1) or Au nanoparticles, can provide mechanistic information pertaining to reactive atom migrations within the assembly. The syntheses of each of these compounds called upon Grignard coupling chemistry, which was activated by Li 2 CuCl 4 . Applicable deuterium containing fragments were either commercially obtained or constructed from by way of an inexpensive and efficient ring opening, protection and dimerization of THF-d 8 . Sulfur incorporation was by thiolacetate substitution or addition reactions. The protocols presented possess general applicability in a number of syntheses requiring block-deuterated fattyalkyl sections.

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