2003-06-01, English, Article, Journal or magazine article edition: Cyclization of 5-hexenyl radicals from nitroxyl radical additions to 4-pentenylketenes and from the acyloin reaction.(Author Abstract) Henry-Riyad, Huda; Tidwell, Thomas T.

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Physical Description
  • Author Abstract
  • Magazine/​Journal article
Published
  • NRC Research Press, 2003 June
Language
  • English

Edition details

Title
  • Cyclization of 5-hexenyl radicals from nitroxyl radical additions to 4-pentenylketenes and from the acyloin reaction.(Author Abstract)
Also Titled
  • Cyclization of 5-hexenyl radicals from nitroxyl radical additions to 4-pentenylketenes and from the acyloin reaction.
Appears In
  • Canadian Journal of Chemistry, v.81, no.6, 2003 June, p.697(8) (ISSN: 0008-4042)
Author
  • Henry-Riyad, Huda
  • Tidwell, Thomas T.
Published
  • NRC Research Press, 2003 June
Physical Description
  • Author Abstract
  • Magazine/​Journal article
Subjects
Target Audience
  • Academic
Summary
  • Photochemical Wolff rearrangements were used to form 5-substituted-4-pentenylketenes 1a-1d (RCH=​CHC[H.sub.2]XC[H.sub.2]CH=​C=​O: 1a R =​ H, X =​ C[H.sub.2]; 1b R =​ Ph, X =​ C[H.sub.2]; 1c R =​ c-Pr, X =​ C[H.sub.2]; 1d R =​ H, X =​ O), which were observed by IR at 2121, 2120, 2119, and 2126 cm-l, respectively, as relatively long-lived species at room temperature in hydrocarbon solvents. These reacted with the nitroxyl radical tetramethylpiperidinyloxyl (TEMPO, TO) forming carboxy-substituted 5-hexenyl radicals 3, which were trapped by a second nitroxyl radical forming 1,2 diaddition products 4a-4d. On thermolysis, 4a-4d underwent reversible reformation of the radicals 3, which underwent cyclization forming cyclopentanecarboxylic acid derivatives 6 or 11 as the major products. However, in the case of 1b, the cyclopentane derivative was formed reversibly and on prolonged reaction times the only product isolated was PhCH=​CH(C[H.sub.2])[sub.4]C[O.sub.2]H (8b) from hydrogen transfer to C[beta] and cleavage of the TEMPO group. Cyclopropylcarbinyl radical ring opening in the cyclized radical 5c from 1c led to the 2-(4-N-tetramethylpiperidinyloxybut-l-enyl)cyclopentane derivative 11 as the major product. In a test for 5-hexenyl radical ring closure in the radical anion intermediate of the acyloin condensation, the ester C[H.sub.2]=​CH(C[H.sub.2])[sub.3]C[O.sub.2]Et (12a) gave the acyloin 13a (76%) as the only observed product, while PhCH=​CH(C[H.sub.2])[sub.3]C[O.sub.2]C[H.sub.3] (12b) with Na in toluene gave 21% of the acyloin product 13b and 42% of 2-benzylcyclopentanol (15) from cyclization of the intermediate radical anion. Key words: ketenes, free radical cyclization, TEMPO, acyloin condensation.
Terms of Use
  • COPYRIGHT 2003 NRC Research Press
Language
  • English
Database
  • Gale Academic OneFile
  • Gale General OneFile
  • Gale Expanded Academic
Identifier
  • 109178891

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Australian Nuclear Science and Technology Organisation. ANSTO Library. Not open to the public Periodical; Journal, magazine, other English; French
Bialik College. Bialik College Library. Not open to the public Periodical; Journal, magazine, other English; French
CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
Cumberland Council. Auburn Library. Open to the public Periodical; Journal, magazine, other English; French
Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
Department of Agriculture and Fisheries Qld. Dept of Agriculture and Fisheries Qld Research Information Service. Not open to the public STACK; vol.29,no.1-v.31; 1951-1953 Periodical; Journal, magazine, other English; French
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James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
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The University of Melbourne. The University of Melbourne Library. Open to the public Ch P CANA; v.29-v.84; 1951-2006 Periodical; Journal, magazine, other English; French
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University of Adelaide. Barr Smith Library. Open to the public 9996397001811; MICROFICHE PER 86; v.60(1982)-v.69(1991) Periodical; Journal, magazine, other English; French
University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
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National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
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These 16 locations in New South Wales:

Library Access Call number(s) Formats held Language
Australian Nuclear Science and Technology Organisation. ANSTO Library. Not open to the public Periodical; Journal, magazine, other English; French
Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
Cumberland Council. Auburn Library. Open to the public Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
Shellharbour City Council. Shellharbour City Library Service. Open to the public Periodical; Journal, magazine, other English; French
Shore School. Boer War Contingent Memorial Library. Not open to the public Periodical; Journal, magazine, other English; French
Southern Cross University. University Library Lismore. Open to the public Electronic resource - Check catalogue for holdings Periodical; Journal, magazine, other English; French
State Library of NSW. Open to the public Held; 1951-1991 Periodical; Journal, magazine, other English; French
St Vincent's Hospital (Sydney). Walter McGrath Library. Not open to the public (EbpS)ebs515368; held Periodical; Journal, magazine, other English; French
The University of Sydney. University of Sydney Library. Open to the public .b1156507x; held Periodical; Journal, magazine, other English; French
University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
University of Wollongong. University of Wollongong Library. Open to the public Online access. Not available for document delivery Periodical; Journal, magazine, other English; French
Western Sydney University. Campbelltown Campus Library. Open to the public 399266; 540.5 4 Periodical; Journal, magazine, other English; French
Western Sydney University. Penrith Campus Library. Open to the public 399266; Online version Periodical; Journal, magazine, other English; French
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Department of Agriculture and Fisheries Qld. Dept of Agriculture and Fisheries Qld Research Information Service. Not open to the public STACK; vol.29,no.1-v.31; 1951-1953 Periodical; Journal, magazine, other English; French
James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
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Flinders University. Flinders University Central Library. Open to the public 9957369701771; 540.5 C21 Periodical; Journal, magazine, other English; French
University of Adelaide. Barr Smith Library. Open to the public 9996397001811; MICROFICHE PER 86; v.60(1982)-v.69(1991) Periodical; Journal, magazine, other English; French
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Bialik College. Bialik College Library. Not open to the public Periodical; Journal, magazine, other English; French
CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
The University of Melbourne. The University of Melbourne Library. Open to the public Ch P CANA; v.29-v.84; 1951-2006 Periodical; Journal, magazine, other English; French
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