{
  "abstract": "The electrocyclic ring opening of azomethine ylides driven by charge neutralization leads to 2-N-acylamino-1,3-diene products. The requisite azomethine ylide is formed by deprotonation of an oxazolinium ion, which is formed by O-silylation of a readily available oxazolidinone starting material. Computational studies indicate that the deprotonation event is the rate limiting step of the sequence providing a short-lived ylide intermediate that opens spontaneously via a low-barrier (1.7 kcal/mol) transition state leading to an enecarbamate product that is about 48 kcal/mol lower in energy than the ylide intermediate. Charge minimization biases the equilibrium position of the electrocyclization reaction leading to the ring-opened product. This transformation provides a straightforward route to 2-Nsubstituted-N-acylamino-1,3-dienes which were used in subsequent Diels-Alder cycloaddition reactions to give cyclohexenecarbamate products.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "name": "Yash Punjabi"
    },
    {
      "name": "Tarun Roy"
    },
    {
      "name": "Roland Tóbiás"
    },
    {
      "name": "Bill Poirier"
    },
    {
      "name": "Matthias Brewer"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/f3wxba7h2hm23.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15009946/v1",
  "fulltext_url": null,
  "id": "f3wxba7h2hm23",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009946/v1",
  "language": null,
  "licence": "CC-BY-NC-ND",
  "licence_label": "CC BY-NC-ND",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Organic Chemistry Cycloaddition Reactions"
    ]
  ],
  "openalex": "W7220697602",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15009946/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-05",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/f3wxba7h2hm23.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:22Z",
      "native_id": "10.26434/chemrxiv.15009946",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009946/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organic Chemistry Cycloaddition Reactions",
      "subfield": "organic"
    }
  ],
  "title": "A Charge-Directed Electrocyclic Ring Opening of Azomethine Ylides as a Route to 2-(N-Acylamino)-1,3-dienes",
  "title_text": "A Charge-Directed Electrocyclic Ring Opening of Azomethine Ylides as a Route to 2-(N-Acylamino)-1,3-dienes",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:22Z",
  "url": "https://research.draconitic.com/paper/f3wxba7h2hm23",
  "venue": "ChemRxiv",
  "versions": []
}