Triangular acid

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Structural formula
Structural formula of triangular acid
General
Surname Triangular acid
other names
  • 1,2-dihydroxycyclopropen-3-one ( IUPAC )
  • Dihydroxycyclopropenone
  • Delta acid
  • Triangelic acid
Molecular formula C 3 H 2 O 3
External identifiers / databases
CAS number 54826-91-4
PubChem 11679790
ChemSpider 9854518
Wikidata Q2823256
properties
Molar mass 86.05 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triangular acid is a chemical compound with the chemical formula C 3 O (OH) 2 from the group of oxocarbon acids and oxocarbons . Their salts and esters are called deltates .

Extraction and presentation

Triangular acid was first obtained in 1975 by photolysis of the bis (trimethylsilyl) squarate by David Eggerding and Robert West , the ester being converted into bis (trimethylsilyl) delta by releasing a carbonyl group (CO) from the ring, which is decomposed by butanol gives the triangular acid.

It can also be prepared by reacting bis (trimethylsilyl) squarate and trimethylsilyl chloride.

Also possible is the synthesis by reaction of dichlorocarbene with bis-tert-butoxyacetylen via triangle acid bis tert -butyl ester.

properties

The resonance structures for the triangular acid dianion suggest that the compound should be aromatic in character .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Eberhard Breitmaier, Günther Jung: Organic Chemistry, 7th complete revision. u. exp. Edition 2012 Basics, classes of compounds, reactions, concepts, molecular structure, natural substances, synthesis planning, sustainability . Georg Thieme Verlag, 2014, ISBN 3-13-159987-1 , p. 575 ( limited preview in Google Book search).
  3. ^ A b Houben-Weyl Methods of Organic Chemistry Vol. E 15/2, 4th Edition Supplement Ene-X and Yne-X Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-181884-0 , p. 1475 ( limited preview in Google Book Search).
  4. ^ David Eggerding, Robert West: Synthesis of dihydroxycyclopropenone (deltic acid). In: Journal of the American Chemical Society. 97, 1975, p. 207, doi : 10.1021 / ja00834a047 .
  5. ^ David Eggerding, Robert West: Synthesis and properties of deltic acid (dihydroxycyclopropenone) and the deltate ion. In: Journal of the American Chemical Society. 98, 1976, p. 3641, doi : 10.1021 / ja00428a043 .
  6. ^ MT Reetz, G. Neumeier, M. Kaschube: Thermal rearrangement of squaric acid bis (trimethylsilyl) ester. In: Tetrahedron Letters 16, 1975, p. 1295, doi : 10.1016 / S0040-4039 (00) 72653-0 .
  7. ↑ Entry on triangular acid. In: Römpp Online . Georg Thieme Verlag, accessed on September 12, 2018.