By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of growth in Heterocyclic Chemistry (PHC) is the fourteenth annual assessment of the literature, masking the paintings released on very important heterocyclic ring structures in the course of 2001. during this quantity there are really expert experiences. the 1st, via Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, through David Knight, discusses five- endo -trig iodocyclisations. the next chapters, prepared by means of expanding heterocycle ring measurement, assessment fresh advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.
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Extra info for A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics
Alternatively, the substrate 64 may be just too simple in the sense that it lacks a distal alkene substituent and hence 4-exo cyclization is favoured. This is certainly the case when using bis(sym-collidine)iodine(I) perchlorate in dichloromethane at -20~ when the alcohol 64 is converted instead into the oxetane 66 <88S862>. Similarly, 3-buten-l-ol is converted into a mixture of oxetane 67 and 3-iodotetrahydrofuran while the ot,ot-dimethyl derivative gives exclusively the oxetane 68. Further examples suggest this may be a feature of such distally unsubstituted 3-buten-l-ols.
Formation of the latter isomer 176 also shows the same preference for a transition state conformation in which the substituent or-to the nucleophilic centre occupies the axial position [99 and 143]. g. 177]. Once again, Baldwin's rules apply when there is competition between 5-exo- and 5-endotrig cyclizations. Thus, exposure of the amino alcohol derivative 178 to iodine in acetonitrile gives only the amino-tetrahydrofuran 180 via intermediate 179 and not the corresponding pyrrolidine <98TL8909>.
For example, the dialkyl substituted precursor 187 gave essentially only the 2,5-trans pyrrolidine 188 using PhSeC1 in dichloromethane at -78~ for lh. Under the same conditions, the phenyl substituted substrate 189 gave a mixture of products. However, the 2,5-trans kinetic product [188; Ph in place of C5Hll] was obtained by adding potassium carbonate as an acid quench and 5 mol% water followed by warming to ambient temperature. The corresponding 2,5-cis isomer 190 was secured by addition of a catalytic amount of 10M hydrochloric acid.