A Convenient One-pot Synthesis of Unsymmetrical Selenium Compounds Using Bis(trimethylsilyl) Selenide

Name: Work Video:
Duration: 3 min 30 s
Description: Abstract The reaction of bis(trimethylsilyl) selenide with n-BuLi followed by alkylation with an R1X gave alkyl silyl selenides. The repetition of a similar one-pot operation with the second n-BuLi and R2X yielded unsymmetrical selenides (R1SeR2) in good yields. This one-pot procedure could be also applicable to the syntheses of selenolesters, selenolcarbonates, and a phosphinothioyl selenide.
Masahito Segi; Masakazu Kato; Tadashi Nakajima; Sohei Suga; Noboru Sonoda
{'id': 'https://openalex.org/W2003730803', 'doi': 'https://doi.org/10.1246/cl.1989.1009', 'title': 'A Convenient One-pot Synthesis of Unsymmetrical Selenium Compounds Using Bis(trimethylsilyl) Selenide', 'display_name': 'A Convenient One-pot Synthesis of Unsymmetrical Selenium Compounds Using Bis(trimethylsilyl) Selenide', 'publication_year': 1989, 'publication_date': '1989-06-01', 'ids': {'openalex': 'https://openalex.org/W2003730803', 'doi': 'https://doi.org/10.1246/cl.1989.1009', 'mag': '2003730803'}, 'language': 'en', 'primary_location': {'is_oa': False, 'landing_page_url': 'https://doi.org/10.1246/cl.1989.1009', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S90825563', 'display_name': 'Chemistry Letters', 'issn_l': '0366-7022', 'issn': ['0366-7022', '1348-0715'], 'is_oa': False, 'is_in_doaj': False, 'is_core': True, 'host_organization': 'https://openalex.org/P4310311648', 'host_organization_name': 'Oxford University Press', 'host_organization_lineage': ['https://openalex.org/P4310311647', 'https://openalex.org/P4310311648'], 'host_organization_lineage_names': ['University of Oxford', 'Oxford University Press'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}, 'type': 'article', 'type_crossref': 'journal-article', 'indexed_in': ['crossref'], 'open_access': {'is_oa': False, 'oa_status': 'closed', 'oa_url': None, 'any_repository_has_fulltext': False}, 'authorships': [{'author_position': 'first', 'author': {'id': 'https://openalex.org/A5042824767', 'display_name': 'Masahito Segi', 'orcid': 'https://orcid.org/0000-0002-3652-2439'}, 'institutions': [{'id': 'https://openalex.org/I10091056', 'display_name': 'Kanazawa University', 'ror': 'https://ror.org/02hwp6a56', 'country_code': 'JP', 'type': 'education', 'lineage': ['https://openalex.org/I10091056']}], 'countries': ['JP'], 'is_corresponding': False, 'raw_author_name': 'Masahito Segi', 'raw_affiliation_strings': ['Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920'], 'affiliations': [{'raw_affiliation_string': 'Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920', 'institution_ids': ['https://openalex.org/I10091056']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5112180887', 'display_name': 'Masakazu Kato', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I10091056', 'display_name': 'Kanazawa University', 'ror': 'https://ror.org/02hwp6a56', 'country_code': 'JP', 'type': 'education', 'lineage': ['https://openalex.org/I10091056']}], 'countries': ['JP'], 'is_corresponding': False, 'raw_author_name': 'Masakazu Kato', 'raw_affiliation_strings': ['Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920'], 'affiliations': [{'raw_affiliation_string': 'Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920', 'institution_ids': ['https://openalex.org/I10091056']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5102920780', 'display_name': 'Tadashi Nakajima', 'orcid': 'https://orcid.org/0000-0003-3827-7171'}, 'institutions': [{'id': 'https://openalex.org/I10091056', 'display_name': 'Kanazawa University', 'ror': 'https://ror.org/02hwp6a56', 'country_code': 'JP', 'type': 'education', 'lineage': ['https://openalex.org/I10091056']}], 'countries': ['JP'], 'is_corresponding': False, 'raw_author_name': 'Tadashi Nakajima', 'raw_affiliation_strings': ['Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920'], 'affiliations': [{'raw_affiliation_string': 'Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920', 'institution_ids': ['https://openalex.org/I10091056']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5109175069', 'display_name': 'Sohei Suga', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I10091056', 'display_name': 'Kanazawa University', 'ror': 'https://ror.org/02hwp6a56', 'country_code': 'JP', 'type': 'education', 'lineage': ['https://openalex.org/I10091056']}], 'countries': ['JP'], 'is_corresponding': False, 'raw_author_name': 'Sohei Suga', 'raw_affiliation_strings': ['Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920'], 'affiliations': [{'raw_affiliation_string': 'Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa UniversityKodatsuno, Kanazawa 920', 'institution_ids': ['https://openalex.org/I10091056']}]}, {'author_position': 'last', 'author': {'id': 'https://openalex.org/A5078826041', 'display_name': 'Noboru Sonoda', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I98285908', 'display_name': 'Osaka University', 'ror': 'https://ror.org/035t8zc32', 'country_code': 'JP', 'type': 'education', 'lineage': ['https://openalex.org/I98285908']}], 'countries': ['JP'], 'is_corresponding': False, 'raw_author_name': 'Noboru Sonoda', 'raw_affiliation_strings': ['Department of Applied Chemistry, Faculty of Engineering, Osaka UniversitySuita 565'], 'affiliations': [{'raw_affiliation_string': 'Department of Applied Chemistry, Faculty of Engineering, Osaka UniversitySuita 565', 'institution_ids': ['https://openalex.org/I98285908']}]}], 'institution_assertions': [], 'countries_distinct_count': 1, 'institutions_distinct_count': 2, 'corresponding_author_ids': [], 'corresponding_institution_ids': [], 'apc_list': None, 'apc_paid': None, 'fwci': 1.721, 'has_fulltext': False, 'cited_by_count': 19, 'citation_normalized_percentile': {'value': 0.796862, 'is_in_top_1_percent': False, 'is_in_top_10_percent': False}, 'cited_by_percentile_year': {'min': 85, 'max': 86}, 'biblio': {'volume': '18', 'issue': '6', 'first_page': '1009', 'last_page': '1012'}, 'is_retracted': False, 'is_paratext': False, 'primary_topic': {'id': 'https://openalex.org/T10807', 'display_name': 'Synthesis and characterization of novel inorganic/organometallic compounds', 'score': 0.9996, 'subfield': {'id': 'https://openalex.org/subfields/1604', 'display_name': 'Inorganic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, 'topics': [{'id': 'https://openalex.org/T10807', 'display_name': 'Synthesis and characterization of novel inorganic/organometallic compounds', 'score': 0.9996, 'subfield': {'id': 'https://openalex.org/subfields/1604', 'display_name': 'Inorganic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, {'id': 'https://openalex.org/T11748', 'display_name': 'Organophosphorus compounds synthesis', 'score': 0.9991, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, {'id': 'https://openalex.org/T11931', 'display_name': 'Organoselenium and organotellurium chemistry', 'score': 0.9982, 'subfield': {'id': 'https://openalex.org/subfields/3005', 'display_name': 'Toxicology'}, 'field': {'id': 'https://openalex.org/fields/30', 'display_name': 'Pharmacology, Toxicology and Pharmaceutics'}, 'domain': {'id': 'https://openalex.org/domains/1', 'display_name': 'Life Sciences'}}], 'keywords': [{'id': 'https://openalex.org/keywords/selenide', 'display_name': 'Selenide', 'score': 0.9701977}, {'id': 'https://openalex.org/keywords/trimethylsilyl', 'display_name': 'Trimethylsilyl', 'score': 0.901952}, {'id': 'https://openalex.org/keywords/one-pot-synthesis', 'display_name': 'One-pot synthesis', 'score': 0.44226056}], 'concepts': [{'id': 'https://openalex.org/C2777016790', 'wikidata': 'https://www.wikidata.org/wiki/Q425269', 'display_name': 'Selenide', 'level': 3, 'score': 0.9701977}, {'id': 'https://openalex.org/C185592680', 'wikidata': 'https://www.wikidata.org/wiki/Q2329', 'display_name': 'Chemistry', 'level': 0, 'score': 0.9696499}, {'id': 'https://openalex.org/C2777000832', 'wikidata': 'https://www.wikidata.org/wiki/Q419853', 'display_name': 'Trimethylsilyl', 'level': 2, 'score': 0.901952}, {'id': 'https://openalex.org/C553756173', 'wikidata': 'https://www.wikidata.org/wiki/Q876', 'display_name': 'Selenium', 'level': 2, 'score': 0.892807}, {'id': 'https://openalex.org/C5304478', 'wikidata': 'https://www.wikidata.org/wiki/Q502457', 'display_name': 'Silylation', 'level': 3, 'score': 0.7517325}, {'id': 'https://openalex.org/C164361826', 'wikidata': 'https://www.wikidata.org/wiki/Q177604', 'display_name': 'Alkylation', 'level': 3, 'score': 0.6280931}, {'id': 'https://openalex.org/C2780263894', 'wikidata': 'https://www.wikidata.org/wiki/Q335268', 'display_name': 'Alkyl', 'level': 2, 'score': 0.61917967}, {'id': 'https://openalex.org/C178790620', 'wikidata': 'https://www.wikidata.org/wiki/Q11351', 'display_name': 'Organic chemistry', 'level': 1, 'score': 0.5069699}, {'id': 'https://openalex.org/C155647269', 'wikidata': 'https://www.wikidata.org/wiki/Q243455', 'display_name': 'Medicinal chemistry', 'level': 1, 'score': 0.45269942}, {'id': 'https://openalex.org/C118939319', 'wikidata': 'https://www.wikidata.org/wiki/Q903091', 'display_name': 'One-pot synthesis', 'level': 3, 'score': 0.44226056}, {'id': 'https://openalex.org/C161790260', 'wikidata': 'https://www.wikidata.org/wiki/Q82264', 'display_name': 'Catalysis', 'level': 2, 'score': 0.20067006}], 'mesh': [], 'locations_count': 1, 'locations': [{'is_oa': False, 'landing_page_url': 'https://doi.org/10.1246/cl.1989.1009', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S90825563', 'display_name': 'Chemistry Letters', 'issn_l': '0366-7022', 'issn': ['0366-7022', '1348-0715'], 'is_oa': False, 'is_in_doaj': False, 'is_core': True, 'host_organization': 'https://openalex.org/P4310311648', 'host_organization_name': 'Oxford University Press', 'host_organization_lineage': ['https://openalex.org/P4310311647', 'https://openalex.org/P4310311648'], 'host_organization_lineage_names': ['University of Oxford', 'Oxford University Press'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}], 'best_oa_location': None, 'sustainable_development_goals': [], 'grants': [], 'datasets': [], 'versions': [], 'referenced_works_count': 12, 'referenced_works': ['https://openalex.org/W1963600451', 'https://openalex.org/W1977660534', 'https://openalex.org/W1996425316', 'https://openalex.org/W2056548454', 'https://openalex.org/W2067985352', 'https://openalex.org/W2076129991', 'https://openalex.org/W2081972472', 'https://openalex.org/W2084685299', 'https://openalex.org/W2163878612', 'https://openalex.org/W2399112719', 'https://openalex.org/W2950218588', 'https://openalex.org/W3013175491'], 'related_works': ['https://openalex.org/W2768204839', 'https://openalex.org/W2333287256', 'https://openalex.org/W2065805476', 'https://openalex.org/W2059055498', 'https://openalex.org/W2044048658', 'https://openalex.org/W2039462867', 'https://openalex.org/W2023879531', 'https://openalex.org/W2016340017', 'https://openalex.org/W2003730803', 'https://openalex.org/W1973795510'], 'abstract_inverted_index': {'Abstract': [0], 'The': [1, 18], 'reaction': [2], 'of': [3, 20, 48], 'bis(trimethylsilyl)': [4], 'selenide': [5], 'with': [6, 11, 25], 'n-BuLi': [7, 28], 'followed': [8], 'by': [9], 'alkylation': [10], 'an': [12], 'R1X': [13], 'gave': [14], 'alkyl': [15], 'silyl': [16], 'selenides.': [17], 'repetition': [19], 'a': [21, 52], 'similar': [22], 'one-pot': [23, 39], 'operation': [24], 'the': [26, 46], 'second': [27], 'and': [29, 51], 'R2X': [30], 'yielded': [31], 'unsymmetrical': [32], 'selenides': [33], '(R1SeR2)': [34], 'in': [35], 'good': [36], 'yields.': [37], 'This': [38], 'procedure': [40], 'could': [41], 'be': [42], 'also': [43], 'applicable': [44], 'to': [45], 'syntheses': [47], 'selenolesters,': [49], 'selenolcarbonates,': [50], 'phosphinothioyl': [53], 'selenide.': [54]}, 'cited_by_api_url': 'https://api.openalex.org/works?filter=cites:W2003730803', 'counts_by_year': [{'year': 2024, 'cited_by_count': 2}, {'year': 2021, 'cited_by_count': 1}, {'year': 2020, 'cited_by_count': 1}, {'year': 2013, 'cited_by_count': 1}], 'updated_date': '2024-12-16T20:00:32.324502', 'created_date': '2016-06-24'}
Publication Information

Basic Information

Access and Citation

AI Researcher Chatbot

Primary Location

Authors

Topics

Keywords

Related Works
