Attempted Synthesis of Bowl-Shaped Polycyclic Aromatic Hydrocarbons via Oxidative Electrocyclization. Products from the Dications of Dibenzo [g, p] chrysene, Tetrabenzo[5.5]fulvalene, and Diphenylmethylidenefluorene
Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C 60 surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF 5 /SO 2 CIF. Compounds 2 and 3 were oxidized to dications...
Saved in:
| Published in: | Polycyclic aromatic compounds Vol. 12; no. 4; pp. 239 - 247 |
|---|---|
| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Taylor & Francis Group
01-04-1998
|
| Subjects: | |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C
60
surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF
5
/SO
2
CIF. Compounds 2 and 3 were oxidized to dications which then underwent a single cyclization to give precursors to 1. Compound 4 underwent two oxidative cyclizations to give a precursor to 1. AM1 calculations of the possible products from cyclization were consistent with preferential formation of the cyclized product with the lower ΔHf. Oxidative cyclization may offer a one-pot synthetic alternative for the preparation of unusual polycyclic aromatic hydrocarbons. |
|---|---|
| AbstractList | Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C
60
surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF
5
/SO
2
CIF. Compounds 2 and 3 were oxidized to dications which then underwent a single cyclization to give precursors to 1. Compound 4 underwent two oxidative cyclizations to give a precursor to 1. AM1 calculations of the possible products from cyclization were consistent with preferential formation of the cyclized product with the lower ΔHf. Oxidative cyclization may offer a one-pot synthetic alternative for the preparation of unusual polycyclic aromatic hydrocarbons. |
| Author | Lowery, John A. Mills, Nancy S. Hensen, Antoinette Malandra, James L. |
| Author_xml | – sequence: 1 givenname: Nancy S. surname: Mills fullname: Mills, Nancy S. organization: Department of Chemistry , Trinity University – sequence: 2 givenname: James L. surname: Malandra fullname: Malandra, James L. organization: Department of Chemistry , Trinity University – sequence: 3 givenname: Antoinette surname: Hensen fullname: Hensen, Antoinette organization: Department of Chemistry , Trinity University – sequence: 4 givenname: John A. surname: Lowery fullname: Lowery, John A. organization: Department of Chemistry , Trinity University |
| BookMark | eNqFkc9O3DAQhy1EJf71AXrzA5CtHTvZrNTLFmiphAQS9IRQ5NjjxpVjR7Z3wbxoX6dm6Q1VnGY033zzO8wR2nfeAUKfKFlQ0pHPlHDStmzVka5mrON0Dx3SpmVVwxjbL33hVVnoDtBRjL8JqWnb1ofozzolmOYECt9ml0aIJmKv8Vf_aKvbUcwF3HibZZbWSLwOfhKpNJdZBS9FGLyLeGsEvn4yqpAt4AsLMhX4YjyXkXcLfBO82sgUsS4HcInB50bu2C7t3Azgnj2-_3WK5wcsx5AjODjFd5CC2LH7ZtE86I3dCrsjwqmizSO4bCdIY7ZGFaDtxodST9AHLWyEj__qMfr57eLu7LK6uv7-42x9VUnGeapWCsSSMEnUoNqOs5pTvoRBLoVgfKC8EUMHujBohxVoqJnipAGlak4E74AdI_p6VwYfYwDdz8FMIuSekv7lM_2bzxRn-eoYp32YxKMPVvVJZOuDDsJJE99afXpKxfzyrsn-H_wX6I6vRA |
| CitedBy_id | crossref_primary_10_1002_ange_200400661 crossref_primary_10_1002_chem_201901450 crossref_primary_10_1021_jo400201z crossref_primary_10_1021_jo981517k crossref_primary_10_1002_anie_200400661 crossref_primary_10_1021_ja0123148 crossref_primary_10_1039_c0cc01730b crossref_primary_10_1021_jo051621j crossref_primary_10_1021_ja711501k |
| Cites_doi | 10.1021/ja00814a034 10.1021/ja00425a018 10.1021/ja00214a031 10.1021/jo00032a053 10.1021/jo00067a049 10.1021/ja00104a074 10.1016/S0040-4020(01)96458-0 10.1039/p19940000779 10.1039/P29900000897 10.1021/ed063p916 10.1351/pac199668020291 10.1021/ja00488a001 10.1016/0040-4020(95)00330-B 10.1080/10406639508009619 |
| ContentType | Journal Article |
| Copyright | Copyright Taylor & Francis Group, LLC 1998 |
| Copyright_xml | – notice: Copyright Taylor & Francis Group, LLC 1998 |
| DBID | AAYXX CITATION |
| DOI | 10.1080/10406639808233841 |
| DatabaseName | CrossRef |
| DatabaseTitle | CrossRef |
| DatabaseTitleList | |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1563-5333 |
| EndPage | 247 |
| ExternalDocumentID | 10_1080_10406639808233841 8233841 |
| Genre | Original Articles |
| GroupedDBID | .7F .QJ 0BK 0R~ 123 1TA 30N 4.4 5VS AAAJW AAAVI AAENE AAJMT AALDU AAMIU AAPUL AAQRR ABBKH ABCCY ABFIM ABHAV ABJVF ABKVM ABLIJ ABOCM ABPEM ABPTK ABQHQ ABTAI ABXUL ACGEJ ACGFS ACGOD ACIWK ACPRK ACTIO ACYAP ADCVX ADGTB ADXPE AEGYZ AEISY AENEX AEOZL AEPSL AEYOC AFKVX AFOLD AFRAH AFWJF AFWLO AGDLA AGMYJ AHDLD AIJEM AIRXU AJWEG AKBVH AKOOK ALMA_UNASSIGNED_HOLDINGS ALQZU AQRUH AVBZW AWYRJ BDVFT BKMSO BLEHA CAG CCCUG CE4 COF CS3 CXCUG DGEBU DKSSO DU5 EAP EBS EJD ESX E~A E~B F5P FUNRP FVPDL GTTXZ HZ~ H~P J.P KYCEM M4Z NA5 NUSFT NW0 O9- OEUFU PQEST PQQKQ RNANH ROSJB RTWRZ S-T SNACF TCY TFL TFT TFW TTHFI TWF UT5 UU3 V1K ZGOLN ~S~ 07J 29O A8Z AAYXX ABDBF ABJNI ABPAQ ABXYU ABZMO ACMLV ADBHG ADOGB AEUXM AGGGY AHDZW AOWVY AWFQP C5E CITATION CTOBV C~V EMK EPL EST ESTFP H13 HF~ HJQDS IPNFZ LJTGL LZ8 OCADI RIG RNS TAV TBQAZ TCCYZ TDBHL TFMCV TUROJ TUS UA2 |
| ID | FETCH-LOGICAL-c344t-9dea703c0dbd684324147ebc7aa34b145ab8efbd6e6b9efe23d405edd240a48e3 |
| IEDL.DBID | TFW |
| ISSN | 1040-6638 |
| IngestDate | Thu Nov 21 23:46:07 EST 2024 Tue Jun 13 19:22:36 EDT 2023 Mon May 13 12:09:16 EDT 2019 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 4 |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c344t-9dea703c0dbd684324147ebc7aa34b145ab8efbd6e6b9efe23d405edd240a48e3 |
| PageCount | 9 |
| ParticipantIDs | crossref_primary_10_1080_10406639808233841 informaworld_taylorfrancis_310_1080_10406639808233841 |
| PublicationCentury | 1900 |
| PublicationDate | 4/1/1998 |
| PublicationDateYYYYMMDD | 1998-04-01 |
| PublicationDate_xml | – month: 04 year: 1998 text: 4/1/1998 day: 01 |
| PublicationDecade | 1990 |
| PublicationTitle | Polycyclic aromatic compounds |
| PublicationYear | 1998 |
| Publisher | Taylor & Francis Group |
| Publisher_xml | – name: Taylor & Francis Group |
| References | CIT0010 CIT0001 CIT0012 Handoo K. L. (CIT0018) 1983; 22 Eliasson B. (CIT0011) 1990; 2 Hagen S. (CIT0004) 1996 CIT0003 CIT0014 CIT0002 CIT0013 CIT0005 CIT0015 Buckles R. E. (CIT0017) 1973; 80 CIT0007 CIT0006 CIT0009 CIT0008 CIT0019 |
| References_xml | – ident: CIT0008 doi: 10.1021/ja00814a034 – ident: CIT0005 doi: 10.1021/ja00425a018 – ident: CIT0006 doi: 10.1021/ja00214a031 – ident: CIT0015 doi: 10.1021/jo00032a053 – volume-title: Novel Syntheses of Bowl-shaped PAHS year: 1996 ident: CIT0004 contributor: fullname: Hagen S. – ident: CIT0007 doi: 10.1021/jo00067a049 – ident: CIT0009 doi: 10.1021/ja00104a074 – ident: CIT0012 doi: 10.1016/S0040-4020(01)96458-0 – volume: 80 start-page: 45 year: 1973 ident: CIT0017 publication-title: Proc. Iowa Acad. Sci. contributor: fullname: Buckles R. E. – ident: CIT0010 doi: 10.1039/p19940000779 – volume: 2 start-page: 897 year: 1990 ident: CIT0011 publication-title: J. Chem. Soc. Perkin Trans doi: 10.1039/P29900000897 contributor: fullname: Eliasson B. – ident: CIT0019 doi: 10.1021/ed063p916 – ident: CIT0002 doi: 10.1351/pac199668020291 – ident: CIT0013 doi: 10.1021/ja00488a001 – volume-title: Calculations were done with the AM1 program contained within Spartan 4.1.1 ident: CIT0014 – ident: CIT0003 doi: 10.1016/0040-4020(95)00330-B – volume: 22 start-page: 909 year: 1983 ident: CIT0018 publication-title: Ind. J. Chem. contributor: fullname: Handoo K. L. – ident: CIT0001 doi: 10.1080/10406639508009619 |
| SSID | ssj0021662 |
| Score | 1.5199348 |
| Snippet | Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C
60
surface, was attempted through oxidative cyclization of... |
| SourceID | crossref informaworld |
| SourceType | Aggregation Database Enrichment Source Publisher |
| StartPage | 239 |
| SubjectTerms | Bowl-shaped polycyclic aromatic hydrocarbons dications diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene |
| Title | Attempted Synthesis of Bowl-Shaped Polycyclic Aromatic Hydrocarbons via Oxidative Electrocyclization. Products from the Dications of Dibenzo [g, p] chrysene, Tetrabenzo[5.5]fulvalene, and Diphenylmethylidenefluorene |
| URI | https://www.tandfonline.com/doi/abs/10.1080/10406639808233841 |
| Volume | 12 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwELagF7jwRmxLkQ-cUFNtEuexhx7a7q72BJV2EUhVtfJjTCNFyWqTpU3_KH-HGXuDWhU4wCmHie0oHnu-sWe-Yey9iWVmTK4CSDUd3YANclA2iBAbQRqJTFlyFGfz7OPXfDwhmpyjPheGwirJh7aeKMLt1bS4pWr6iDh8CjKUo5xuieLcpa0jriGdXky__HK3wjT1d50U4I5q1t9p_q6HO1bpDmfpLWszffqf3_mMPdnCTH7s9eI5ewDVC_botK_u9pL9OG6JlQrxJp93FaLApmh4bflJfVUG80u5QsFZXXa602WhsaPacbvyWWfQ5Mm1Qm3l3wvJP10XxpGH84mvqONa-OTOQ37mCWUbTmksHIfh4_6QkEYbFwqqm5qffzvgqwuuL9ddg5vvAV9Au5ZOdp4cJhd2U-KKcBL8G9iMItO6kspfdyWVRQVbbmpi53zFPk8ni9NZsC3yEOhYiDYYGZC46-ihUSbNiR8wRI1ROpMyFioUiVQ5WJRBqkZgIYoNYkwwBqGIFDnEr9lOVVfwhnEVJkol0mQZOpUhpAhNhdBWCBkPVRSNBuxDP8nLlefyWIZbitR7czVgw9tqsGzdAYr11U7uv75sr9sBS_7SJP7jULv_2G6PPfYZkhRH9JbttOsN7LOHjdm8cyvhJ2kHDJ4 |
| link.rule.ids | 315,782,786,1455,1509,27933,27934,58021,59734,60523 |
| linkProvider | Taylor & Francis |
| linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9NAEF5BOZQL5SlCeeyBE6qr2Lt-5IJUmkRBlFIpQSBVlbWPWWrJsqPYgZo_yt9hxo5RqwIHOPkwHq_tnd157Mw3jL20QsXWJtqDyFDoBpyXgHZegLYRRIGMtSNHcTaPjz8n4wnB5Lzua2EorZJ8aNcBRbR7NS1uCkb3KXF4laQpRwkdE4mE6tZvoWEsCDt_Mf30y-Hyo6g77aQUdxS0_lTzd4-4opeuoJZe0jfTnf9907vszsbS5AedaNxjN6C4z7YP-wZvD9iPg5qAqdDk5POmQEOwyipeOv6m_JZ783O1RMJJmTemMXlm8EFlC-_KZ41FradWGgWWf80U_3CR2RY_nE-6pjotR1ffuc9POkzZilMlC8dh-LiPE9Jo40xD8b3kp1_2-PKMm_NVU-H-u8cXUK9USzsN98Mz_GBcFC0FfweyUXJak1MH7Canzqjg8nVJAJ0P2cfpZHE48zZ9HjwjpKy9kQWFG48ZWm2jhCACfRQabWKlhNS-DJVOwCENIj0CB4GwaGaCtWiNKJmAeMS2irKAx4xrP9Q6VDaO0a_0IULrVErjpFRiqINgNGCv-llOlx2cR-pvUFKvzdWADS_LQVq3MRTXNTy5fntaX9QDFv6FRfxxqCf_yPeCbc8W74_So7fH73bZ7a5gktKKnrKterWGZ-xmZdfP22XxEz59EMI |
| linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9NAEF5BkYBLeYuU1x44obqK7fUjBw6lSRQEKpESBFJVWfuYpZYsO4odqPmj_B1mvDFqVeAAJx_Gs2t5Z3ceO_MNYy9NKBNjUuVBrCl0A9ZLQVkvQNsI4kAkypKjOFskx5_T8YRgcl73tTCUVkk-tHVAEd1ZTZt7ZWyfEYdPQYpylNItUZhS2fqNeOg8quX00y9_y49jd9lJGe4oZ_2l5u-GuKSWLoGWXlA30zv_-aF32e7WzuSHTjDusWtQ3me3jvr2bg_Yj8OGYKnQ4OSLtkQzsM5rXln-pvpWeIszuULCvCpa3eoi1zhQ1YG78llrUOfJtUJx5V9zyT-c56ZDD-cT11Kn43DVnQd87hBla051LByn4eM-SkizjXMF5feKn3zZ56tTrs_WbY2n7z5fQrOWHe0kOohO7abALdFR8G8gG6WmtQX1v24L6osKtthUBM_5kH2cTpZHM2_b5cHToRCNNzIg8djRQ6NMnBJAoI8io3QiZSiULyKpUrBIg1iNwEIQGjQywRi0RaRIIXzEdsqqhMeMKz9SKpImSdCr9CFG21QIbYWQ4VAFwWjAXvWLnK0cmEfmbzFSr6zVgA0vikHWdBEU69qdXH09a86bAYv-whL-caq9f-R7wW7Ox9Ps_dvjd0_YbVctSTlFT9lOs97AM3a9Npvn3ab4Cd5OD2Y |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Attempted+Synthesis+of+Bowl-Shaped+Polycyclic+Aromatic+Hydrocarbons+via+Oxidative+Electrocyclization.+Products+from+the+Dications+of+Dibenzo+%5Bg%2C+p%5D+chrysene%2C+Tetrabenzo%5B5.5%5Dfulvalene%2C+and+Diphenylmethylidenefluorene&rft.jtitle=Polycyclic+aromatic+compounds&rft.au=Mills%2C+Nancy+S.&rft.au=Malandra%2C+James+L.&rft.au=Hensen%2C+Antoinette&rft.au=Lowery%2C+John+A.&rft.date=1998-04-01&rft.pub=Taylor+%26+Francis+Group&rft.issn=1040-6638&rft.eissn=1563-5333&rft.volume=12&rft.issue=4&rft.spage=239&rft.epage=247&rft_id=info:doi/10.1080%2F10406639808233841&rft.externalDocID=8233841 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1040-6638&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1040-6638&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1040-6638&client=summon |