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Benzynes

Term · Chemistry · MLC-T-CHM-001196

1,2-Didehydrobenzene, C6H4, the parent aryne, together with its substituted derivatives. It is a strained, neutral, short-lived intermediate whose formal triple bond consists of the aromatic pi bond plus a weak extra bond formed by in-plane overlap of two sp2 orbitals. Benzynes are generated in situ, for example from 2-(trimethylsilyl)phenyl triflate with fluoride, and are trapped by nucleophiles or in cycloadditions.

Table 1. Record
IdentifierMLC-T-CHM-001196
FieldChemistry
SubjectOrganic and Biomolecular Chemistry
ReferencesPAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1088 (https://doi.org/10.1351/pac199466051077); PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1322 (https://doi.org/10.1351/pac199567081307)
See alsoAryne; Dehydroarenes
Record as JSON
{
  "id": "MLC-T-CHM-001196",
  "term": "Benzynes",
  "field": "Chemistry",
  "definition": "1,2-Didehydrobenzene, C6H4, the parent aryne, together with its substituted derivatives. It is a strained, neutral, short-lived intermediate whose formal triple bond consists of the aromatic pi bond plus a weak extra bond formed by in-plane overlap of two sp2 orbitals. Benzynes are generated in situ, for example from 2-(trimethylsilyl)phenyl triflate with fluoride, and are trapped by nucleophiles or in cycloadditions.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "aryne",
    "dehydroarenes"
  ],
  "references": [
    "PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1088 (https://doi.org/10.1351/pac199466051077)",
    "PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1322 (https://doi.org/10.1351/pac199567081307)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/benzynes/"
}

Record 1,285 of 13,676 in Chemistry terminology (MLC-0109). Request the full dataset.