Summary of Thiol Chemistry

Problem 13.29 Give the IUPAC names for each of the following alcohols. Which are 1°, 2°, and 3°  

Problem 13.30 Write condensed structural formulas and give IUPAC names for (a) vinylcarbinol, (6) diphenylcarbinol, (c) dimethylethylcarbinol, (d) benzylcarbinol. M 

Synthesize each, using a different reaction from among a reduction, an SN2 displacement, a hydration, and a Grignard reaction. M 

Synthesis of the 3° isomer, (i), has restrictions the SN2 displacement of a 3° halide cannot be used because elimination would occur nor is there any starting material that can be reduced to a 3° alcohol. Either of the two remaining methods can be used arbitrarily the Grignard is chosen. 

The Sn2 displacement on the corresponding RX is best for P alcohols such as (ii) and (iii) let us choose (ii) for this synthesis. 

The 1 ° alcohol, (iii), and the 2° alcohol, (iv) can be made by either of the two remaining syntheses. However, the one-step hydration with H30 to give (iv) is shorter than the two-step hydroboration-oxidation to give (iii). 

Problem 13.37 Prepare ethyl p-chlorophenylcarbinol by a Grignard reaction. 

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The conversion of thiols to various sulphenyl derivatives has been utilized as a means of thiol protection as well as, in many cases, a route to disulphides. Sulphenyl derivatives considered in this section include S-sulphonates, sulphenyl iodides, symmetrical and unsymmetrical disulphides (as used for protection) and certain heavy-metal derivatives. A summary of the chemistry of certain sulphenyl derivatives appeared earlier [159]. 

Below, first a brief summary of the state-of-the-art for more traditional design of dendrimers is given, after which we focus on the use of the CuAAC, Diels-Alder cycloaddition reactions and thiol-ene chemistry for the preparation of these dendritic structures. 

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