Syntheses of the pentacyclo[6.3.0.02,6.03,10.05,9]undecyl (trishomocubyl) and tetracyclo[6.3.0.04,11.05,9]undeca-2,6-dienyl (homohypostrophenyl) systems
“…We now describe a variant of this / l 1 procedure even simpler in practice. As before (I), the diketone was reduced to the endo,endo-diol 2 (1,5). The latter was treated with potassium iodide in polyhydrogen fluoride -pyridine, a reagent recently developed by Olah and Welch (6), and the hours, and three products appeared: first the ether 4 ("oxabirdcage" (5,7)) formed rapidly and then dis-1 1 appeared (20% after 2 h, 7% after 7 h, 0% after 24 h); then more slowly, the diiodide 5 and homohypostrophene 6.…”
Section: Introductionmentioning
confidence: 82%
“…Perhaps the simplest of these routes was the threestep procedure (Scheme 1: 1 + 2+ 3-6) of Smith and Barborak (1). We now describe a variant of this / l 1 procedure even simpler in practice.…”
The diol 2 was converted by treatment with potassium iodide in polyhydrogen fluoride – pyridine into a mixture of the diiodide and homohypostrophene 6. The diol 10 under the same conditions gave the ether 14. Treatment of the mixture of 5 and 6 with sodium in boiling tetrahydrofuran gave an easily-separable mixture of 6 and 7.
“…We now describe a variant of this / l 1 procedure even simpler in practice. As before (I), the diketone was reduced to the endo,endo-diol 2 (1,5). The latter was treated with potassium iodide in polyhydrogen fluoride -pyridine, a reagent recently developed by Olah and Welch (6), and the hours, and three products appeared: first the ether 4 ("oxabirdcage" (5,7)) formed rapidly and then dis-1 1 appeared (20% after 2 h, 7% after 7 h, 0% after 24 h); then more slowly, the diiodide 5 and homohypostrophene 6.…”
Section: Introductionmentioning
confidence: 82%
“…Perhaps the simplest of these routes was the threestep procedure (Scheme 1: 1 + 2+ 3-6) of Smith and Barborak (1). We now describe a variant of this / l 1 procedure even simpler in practice.…”
The diol 2 was converted by treatment with potassium iodide in polyhydrogen fluoride – pyridine into a mixture of the diiodide and homohypostrophene 6. The diol 10 under the same conditions gave the ether 14. Treatment of the mixture of 5 and 6 with sodium in boiling tetrahydrofuran gave an easily-separable mixture of 6 and 7.
“…[I3-' 81 The requirements of preparative metal atom chemistry clearly favor the q6: q4-structure type for benzene and toluene." 6 , 71 In contrast to this, the stable bis(hexamethy1benzene)iron has an q6 :q6-structure, and can be prepared by classical methods. ["] In a number of cases, a three component reaction of Fe(g) with arenes and ligands L has proved to be an alternative for the formation of [(arene)FeL,] complexes."…”
In 1969, P. L. Timms reported the first preparative cocondensation reactions of metal vapors with organic and inorganic substrates. The use of this technique in preparative chemistry soon spread rapidly, but in recent years there has been less activity in this sector. If metal atom reactions are not utilized primarily for the formation of new products, but for the synthesis of highly reactive intermediates, a new synthetic strategy may be developed. Our aims are reaction sequences which, based on an effective cocondensation reaction, lead gradually and selectively to new substance classes. This principle can be illustrated by the example of the cocondensation products of arenes and iron, cobalt, or nickel vapor, which decompose between -70 and -50°C. The classes of products accessible by this method extend from clusters, through x-complexes, organophosphorus and organoboron cage compounds to pure organic cycloaddition products.
“…-In den Schemata 2') und 3 sind die bewahrten Vorgehensweisen skizziert, nach denen Hypostrophen l a [12], auch nach verbessertem Verfahren [13] noch immer recht aufwendig in der Herstellung, und die gut zuganglichen Homologen l b [ 101 [14] [15] und lc [ l l ] einfach bzw. zweifach benzo-anelliert wurden.…”
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