By Arthur Israel Vogel
The most effective books there's instructing useful natural chemistry. The 3rd version of this e-book (first released in 1956) is de facto of far better use to the pastime chemist, because it doesn't utilize any hideously dear glassware/apparatus or unique reagents or catalysts.
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Additional resources for A text-book of practical organic chemistry, including qualitative organic analysis
However, if chloromethylation is carried out with an excess (> 2 molcs) of aluminium chloride, coordination between the latter and the carbonyl group increases -M electron withdrawal, which lowers the reactivity of the 5 position below that of the 4 position, so that 4-substitution predominates in the proportion 4 . z16 MeCO a : H . l I 30 Me There have three reports of chloroalkylation. This reaction takes place less readily because the extra alkyl group (or groups) delocalizes the positive charge away from the electrophilic center.
A) Calculated on the assumption that additivity holds. ( b ) These values arc not a true measure of the electronic effect of the M e 0 substituent because it is quite strongly hydrogen-bonded. The detritiation of thiophene and a number of substituted thiophenes in TFAHOAc mixtures was also studied by Butler and E a b ~ r n . 8"C. 1 unit, since the strongest acid (in which bonding is more severe) was only used for the least reactive compounds, and in these bonding would be less important because of the reduced electron density in the thiophene ring.
This is partly because of the lack of side reactions resulting in good yields but also because many of the products and their derivatives are of considerable pharmacological importance. Aminomethylation and chloroalkylation are treated separately from alkylation because each reaction has quite distinct conditions and points of interest, and the same is true of formylation compared to other acylations, which are likewise considered separately. 34 Roger Taylor A . 16' Relatively little work has been reported ir, recent years.
A text-book of practical organic chemistry, including qualitative organic analysis by Arthur Israel Vogel