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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Structural Reevaluation of the Crystalline Methylenedigallic Acids

Sebastian M. Marcuccio A B and Kathleen A. Turner A C
+ Author Affiliations
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A CSIRO Manufacturing Flagship, Private Bag 10, Clayton South MDC, Vic. 3169, Australia.

B Current address: Advanced Molecular Technologies Pty Ltd, Unit 1, 7-11 Rocco Drive Scoresby, Vic. 3179, Australia.

C Corresponding author. Email: kathleen.turner@csiro.au

Australian Journal of Chemistry 69(1) 8-11 https://doi.org/10.1071/CH15120
Submitted: 12 March 2015  Accepted: 18 May 2015   Published: 30 June 2015

Abstract

Analysis of the products of the previously reported conditions for the preparation of crystalline methylenedigallic acids from gallic acid has revealed that the water-insoluble acid is a tetrahomodioxacalix[4]arene and the water-soluble acid is a trimeric species.


References

[1]  The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals, 13th ed. (Eds M. J. O’Neil, A. Smith, P. E. Heckelman, S. Budayari) 2001 (Merck: Whitehouse Station, N.J.); The Merck Index available at: https://www.rsc.org/merck-index.

[2]  R. Möhlau, L. Kahl, Ber. Dtsch. Chem. Ges. 1898, 31, 259.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  N. Caro, Ber. Dtsch. Chem. Ges. 1892, 25, 939.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  D. Bhattacharjee, F. D. Popp, J. Heterocycl. Chem. 1980, 17, 315.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXlvVKjtL0%3D&md5=ba5194c469f13a97f92399bc9edb5cafCAS |

[5]  J. B. Hendrickson, P. M. DeCapite, J. Org. Chem. 1985, 50, 2112.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXktVGqtbs%3D&md5=358f0e49bb5720f180f4500ed28a4dfcCAS |

[6]  A. G. S. Hoegberg, J. Am. Chem. Soc. 1980, 102, 6046.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXls1OntLo%3D&md5=8cc8ba57328bb6b4900b3939506a1de6CAS |

[7]  L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Helgeson, C. B. Knobler, D. J. Cram, J. Org. Chem. 1989, 54, 1305.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXhtlCrtLk%3D&md5=57d00b15157343d89106425224c174b9CAS |