{"id":"W1986758945","doi":"10.1021/jo802343k","title":"A New Synthetic Route to 3-Oxo-4-amino-1,2,3-oxadiazole from the Diazeniumdiolation of Benzyl Cyanide: Stable Sydnone Iminium <i>N</i>-Oxides","year":2009,"lang":"en","type":"article","venue":"The Journal of Organic Chemistry","topic":"N-Heterocyclic Carbenes in Organic and Inorganic Chemistry","field":"Chemistry","cited_by":18,"is_retracted":false,"has_abstract":true,"ca_institutions":"McGill University","funders":"","keywords":"Sydnone; Chemistry; Tautomer; Oxadiazole; Salicylaldehyde; Iminium; Medicinal chemistry; Reactivity (psychology); Hydroxide; Benzonitrile; Cyanide; Organic chemistry; Polymer chemistry; Schiff base; Catalysis; Ring (chemistry)","routes":{"ca_aff":true,"ca_fund":false,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.00006319617,0.0002458931,0.0001031236,0.0001345371,0.0001434184,0.0001232605,0.0002836026,0.0001967638,0.001456733],"category_scores_gemma":[0.00006387328,0.0001117596,0.0001090219,0.0001026779,0.0001501622,0.0001768857,0.0001622982,0.0004372415,0.0005111856],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001939023,"about_ca_system_score_gemma":0.0003779896,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0006756806,"about_ca_topic_score_gemma":0.002336344,"domain_scores_codex":[0.9999632,0.000003025714,0.000003351839,0.00001065655,0.00001051612,0.000009345695],"domain_scores_gemma":[0.9999692,0.000002470992,0.000006246838,0.000004179156,0.000006595083,0.00001133009],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.00002084465,0.00002007555,0.00007507185,0.00008730464,0.000002939753,0.0001521874,0.00003935207,0.00005963974,0.9935091,0.000822745,0.0001471525,0.005063461],"study_design_scores_gemma":[0.00004442716,0.0007508511,0.002049484,0.00001444717,0.00001328999,0.001215392,0.00004783661,0.0006049292,0.9600983,0.0003255369,0.03482002,0.0000155071],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.8830502,0.005670805,0.07917641,0.0007353289,0.0005622265,0.0003706958,0.001140901,0.0005837854,0.02870958],"genre_scores_gemma":[0.9493321,0.002965964,0.03467516,0.0001401933,0.00003549827,0.0001001975,0.0005748624,0.00003709212,0.01213885],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.001456733,"threshold_uncertainty_score":0.004873276,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.007395024687360254,"score_gpt":0.2125134945921011,"score_spread":0.2051184699047408,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}