{"doi":"10.1002/chem.19970030514","title":"Synthesis of 1,2,3,4‐Bisiminofullerene and 1,2,3,4‐Bis(triazolino)fullerene—on the Mechanism of the Addition Reactions of Organic Azides to [60]Fullerene","abstract":"<jats:title>Abstract</jats:title><jats:p>The reactions of organic azides with [60]fullerene have paved the way for the synthesis of adducts with a variety of structures. Treatment of [60]fullerene with 2,2‐dibenzyl‐1,3‐diazidopropane (<jats:bold>10</jats:bold>) in refluxing chlorobenzene afforded three products, namely, <jats:bold>8, 9</jats:bold>, and <jats:bold>11</jats:bold> in 18, 25, and 11% yields, respectively. Thermolysis of <jats:bold>9a</jats:bold> in refluxing chlorobenzene gave a 40:54:6 mixture of <jats:bold>8, 11</jats:bold>, and C<jats:sub>60</jats:sub> in quantitative yield. No interconversion between <jats:bold>8</jats:bold> and <jats:bold>11</jats:bold> was observed. Whereas <jats:bold>11</jats:bold> was stable towards thermolysis, <jats:bold>8</jats:bold> decomposed to C<jats:sub>60</jats:sub> (35% yield) on refluxing in chlorobenzene for 24 h, but it did not produce any <jats:bold>11</jats:bold>. This indicates that <jats:bold>9a</jats:bold> is an intermediate in the formation of <jats:bold>8</jats:bold> and <jats:bold>11</jats:bold>. A general mechanism for the addition of azides to C<jats:sub>60</jats:sub> is proposed. A similar mechanistic pathway is suggested for the thermolysis of <jats:bold>9a</jats:bold>.</jats:p>","journal":"Chemistry – A European Journal","year":1997,"id":31483,"datarank":2.2786616337275616,"base_score":3.58351893845611,"endowment":3.58351893845611,"self_citation_contribution":0.5375278407684165,"citation_network_contribution":1.741133792959145,"self_endowment_contribution":0.5375278407684165,"citer_contribution":1.741133792959145,"corpus_percentile":null,"corpus_rank":null,"citation_count":35,"citer_count":33,"citers_with_citation_signal":32,"citers_with_endowment":32,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":168668,"name":"Hsiao‐Hua Yu","orcid":null,"position":1,"is_corresponding":false},{"id":168669,"name":"Chiun‐Gung Juo","orcid":null,"position":2,"is_corresponding":false},{"id":168670,"name":"Kuo‐Ming Chien","orcid":null,"position":3,"is_corresponding":false},{"id":168671,"name":"Guor‐Rong Her","orcid":null,"position":4,"is_corresponding":false},{"id":168672,"name":"Tien‐Yau Luh","orcid":null,"position":5,"is_corresponding":false},{"id":168667,"name":"Clifton K.‐F. Shen","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":3.58351893845611,"endowment":3.58351893845611,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"24523987","pmcid":null,"openalex_id":"https://openalex.org/W1965168651","authors":[],"funders":[],"total_grants":0,"fwci":4.3282,"citation_percentile":0.9452827,"influential_citations":0,"citation_trend":[{"year":2012,"count":3},{"year":2013,"count":1},{"year":2015,"count":1},{"year":2016,"count":2},{"year":2020,"count":1}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.19970030514","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.19970030514","host_type":"publisher"},{"url":"https://doi.org/10.1002/chem.19970030514","host_type":"journal"},{"url":"http://ntur.lib.ntu.edu.tw//handle/246246/166260","host_type":"repository"}],"fields_of_study":["Fullerene Chemistry and Applications","Chemical Reactions and Mechanisms","Carbon Nanotubes in Composites","Chemistry"],"mesh_terms":[],"keywords":["Chlorobenzene","Fullerene","Chemistry","Thermal decomposition","Yield (engineering)","Adduct","Decomposition","Reaction mechanism","Fullerene chemistry","Organic chemistry","Medicinal chemistry","Catalysis","Materials science"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-09T07:18:27.835875Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}