?-Pyrone derivatives

Garkusha, G. A.; Khutornenko, G. A.

doi:10.1007/bf00742356

Cited by 2 publications

(5 citation statements)

References 4 publications

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“…The Merck index 12 reports 270 °C as the decomposition temperature for 1, citing Garkusha and Khutornenko. 11 Undoubtedly, these researchers and others had prepared the furan, 3. 10,14…”

Section: Synthesesmentioning

confidence: 99%

“…The first reported synthesis of 1 was from Thoms and Pietrulla, who hydrolyzed diethylbromocheliodonate ( 2 ) in KOH (Scheme ) . Garkusha and Khutornenko later reported a slight modification by substituting the solvent acetone with dioxane. We employed both procedures and were surprised to find that neither method yielded the orthorhombic crystals of 1 previously described.…”

Section: Synthesesmentioning

confidence: 99%

“…Isomers 1 and 3 , not easily distinguished in a casual spectroscopic analysis, decomposed at discrete temperatures, 285 and 270 °C, respectively, but as decomposition temperatures are typically less well-defined than melting temperatures it is possible to imagine that the latter could have been mistaken for the former. The Merck index 12 reports 270 °C as the decomposition temperature for 1 , citing Garkusha and Khutornenko . Undoubtedly, these researchers and others had prepared the furan, 3 . , …”

Section: Synthesesmentioning

confidence: 99%

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Poppy Acid: Synthesis and Crystal Chemistry

1999

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It had long ago been reported that poppy acid crystals encapsulate and orient a great variety of molecules during solution growth and in so doing seem to egregiously violate the principle of isomorphism. To comprehend this surprising host−guest chemistry, and exploit it for measuring anisotropic molecular properties, we attempted to carry out the oft-used literature synthesis of poppy acid, (3-hydroxy-2,6-dicarboxy-γ-pyrone), but discovered that the standard procedures did not produce the title compound. We instead obtained a constitutional isomer as the potassium salt of 2-oxaloate-3-hydroxy-5-carboxyfuran. Therefore, we designed and carried out the first total synthesis of poppy acid. It crystallizes as either of two polymorphs, an orthorhombic form (Pbca) and a monoclinic form (C2/c), both characterized by weakly bonded layers consistent with perfect cleavages. The great majority of the dyes tested, 15 of 19, produced poppy acid crystals colored in particular growth sectors displaying strong linear dichroism. The observation of pronounced absorption anisotropy is consistent with a general mixed crystal growth mechanism in which the dyes substitute for poppy acid molecules within the layers and are further oriented in the direction of hydrogen bound rows of molecules within layers.

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“…The Merck index 12 reports 270 °C as the decomposition temperature for 1, citing Garkusha and Khutornenko. 11 Undoubtedly, these researchers and others had prepared the furan, 3. 10,14…”

Section: Synthesesmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

See 1 more Smart Citation

Poppy Acid: Synthesis and Crystal Chemistry

1999

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“…Compound 4 was prepared from 3 [3]. The crude product was purified by flash chromatography using ethyl acetate (EtOAc) as the eluent.…”

Section: Experimental General Methodsmentioning

confidence: 99%

“…The conversion of 3 directly into 7 by THF-BH 3 was not performed, since 3 is only partially THF-soluble at lower temperatures. Compound 7 is then transformed into the dibromide 8 or the tosylate 6 by standard procedures.…”

mentioning

confidence: 99%

The chemistry of the highly reactive 2,6‐bis(bromomethyl)‐4‐pyrone

Löwe¹,

Brätter²,

Weber³

et al. 2001

Journal of Heterocyclic Chem

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Under basic conditions 2,6‐bis(bromomethyl)‐4‐pyrone 8 reacts with tetraethylene glycol to yield the unexpected macrocycle 9, which is related to the antibiotic Kjellmanianone 10. We propose that this ring transformation proceeds via the cyclopropyl intermediate d (Scheme 2), which undergoes a ring opening reaction comparable to the Favorskii rearrangement. Also, 8 reacts with methanol/sodium methoxide to yield the 3(2H)‐furanone derivative 11, the formation of which is suggested to proceed via the intermediate k with a carbenium‐oxonium‐ion subunit (Scheme 3). The structure of the 3(2H)‐furanone derivative was confirmed by X‐ray analysis.

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?-Pyrone derivatives

Cited by 2 publications

References 4 publications

Poppy Acid: Synthesis and Crystal Chemistry

Poppy Acid: Synthesis and Crystal Chemistry

The chemistry of the highly reactive 2,6‐bis(bromomethyl)‐4‐pyrone

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