1992
DOI: 10.1039/c39920001733
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Octaamide hemicarcerands

Abstract: The syntheses, characterization (including a crystal structure determination), and limited constrictive binding properties of two octaamide hemicarcerands are reported, as well as a fourfold rearrangement of an acid-acetal to a phenol-lactone-acetal, the crystal structure of which has been determined. ~We previously reported the synthesis and constrictive binding properties of hydrolytically unstable hemicarcerands 11 and 22 with portals and enforced interiors large enough to admit and expel neutral guests at … Show more

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Cited by 26 publications
(13 citation statements)
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“…To gain access to monocarboxycavitand 8, we first tried to directly carboxylate cavitand 1 with carbon dioxide in analogy to the work of Cram et al who synthesized tetracarboxylated cavitands. 9 To our surprise all of our approaches to lithiate 1 or monobrominated 2 and then treat the resulting organolithium compound with carefully dried carbon dioxide 10 only resulted in non-functionalized cavitand 1 in both cases. It seems that carbon dioxide is simply not reactive enough to achieve the desired functionalization of the sterically crowded 1 under the conditions employed.…”
Section: Scheme 2 Synthesis Of Monohalogenated Cavitandsmentioning
confidence: 89%
“…To gain access to monocarboxycavitand 8, we first tried to directly carboxylate cavitand 1 with carbon dioxide in analogy to the work of Cram et al who synthesized tetracarboxylated cavitands. 9 To our surprise all of our approaches to lithiate 1 or monobrominated 2 and then treat the resulting organolithium compound with carefully dried carbon dioxide 10 only resulted in non-functionalized cavitand 1 in both cases. It seems that carbon dioxide is simply not reactive enough to achieve the desired functionalization of the sterically crowded 1 under the conditions employed.…”
Section: Scheme 2 Synthesis Of Monohalogenated Cavitandsmentioning
confidence: 89%
“…However, larger amide cages have been synthesized by multiple bond formations in one step, as well as by the above‐mentioned stepwise approaches. Here, a template effect cannot be exploited and indeed the yields drop substantially, for example, to 7 % for a [2+4] octaamide cage based on resorcinarene tetrakis(acid chlorides) and meta ‐phenylenediamines . For comparison: The structurally related corresponding imine cage is synthesized by DCC in much higher yields of 45 % .…”
Section: Figurementioning
confidence: 99%
“…The external loop airlift reactor (ELALR) has many advantages such as uniform material mixing property, vigorous turbulence, scattered bubbles, large mass transfer area, etc . It is the main piece of equipment for the production of ammonia phosphate.…”
Section: Introductionmentioning
confidence: 99%