2003-06-01, English, Article, Journal or magazine article edition: Intramolecular reactions of dialkoxycarbenes with a carbonyl group.(Author Abstract) Dawid, Malgorzata; Warkentin, John

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

Edition details

Title
  • Intramolecular reactions of dialkoxycarbenes with a carbonyl group.(Author Abstract)
Also Titled
  • Intramolecular reactions of dialkoxycarbenes with a carbonyl group.
Appears In
  • Canadian Journal of Chemistry, v.81, no.6, 2003 June, p.598(9) (ISSN: 0008-4042)
Author
  • Dawid, Malgorzata
  • Warkentin, John
Published
  • NRC Research Press, 2003 June
Physical Description
  • Author Abstract
  • Magazine/​Journal article
Subjects
Target Audience
  • Academic
Summary
  • Thermolysis of 5,5-dimethyl-2-methoxy-2- (2-oxocyclohexylmethoxy)-[DELTA.sup.3]-1,3,4-oxadiazoline (3a) in benzene at 110[degrees]C generated a carbonyl ylide intermediate that gave, in a minor side reaction, a product of 1,3-dipolar cyclo-addition to the carbonyl group. The major fate of the ylide was fragmentation to acetone and a dialkoxycarbene, MeO(RC[H.sub.2]O)C:, where R =​ 2-oxocyclohexyl. The carbene, in turn, underwent overall [2 + 1] cycloaddition to the carbonyl group, presumably to afford diastereomeric dialkoxyoxiranes that could not be isolated. A product of methanolysis of the presumed oxiranes was isolated by GC and its structure was determined by means of X-ray diffraction. Methanol is believed to result from reaction of an intermediate or product with adventitious water. Deliberate hydrolysis of the product of methanolysis gave a hydroxy lactone, the structure of which was also secured by means of single crystal X-ray diffraction. Those structures indicated the likely structures of the oxirane precursors. A second, and major, product from the carbene was a bicyclic ketone. Similar products were obtained from intramolecular reactions of a carbene tethered to cyclopentanone through a two-carbon or a one-carbon tether. Some compounds that are apparently "dimers" of the oxiranes were also isolated and identified by means of X-ray diffraction. These dimers are thought to originate from the reaction of a ring-opened oxirane (a dipole or a cation from electrophilic opening of the oxirane) with a molecule of the oxirane rather than from biomolecular reaction between two oxirane molecules. The oxiranes open by cleavage of the [(RO).sub.2]C--O bond rather than the oxirane C--C bond, the normally observed sense of thermal ring opening. The properties of the carbenes and the presumed oxiranes serve to point out the options available to such intermediates and suggest that some new, synthetically useful reactions may become possible. Key words: bicyclic ketone, dialkoxycarbene, dialkoxyoxirane, hydroxylactone, "oxirane dimers".
Terms of Use
  • COPYRIGHT 2003 NRC Research Press
Language
  • English
Database
  • Gale Academic OneFile
  • Gale General OneFile
  • Gale Expanded Academic
Identifier
  • 109178879

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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
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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); OS; YOS-SER 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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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
University of Tasmania. Open to the public .b10389556; Scien ser v29-74;1951-96 Periodical; Journal, magazine, other English
University of Western Australia. University of Western Australia Library. Open to the public 9944031702101; HELD; V. 76-92 ; 1998-2014; V. 49-75 ; 1971-1997 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 9919157280001571; HELD; Vol. 62, no. 7 (1984) - v. 74 (1996)[Impf.]. 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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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 Held. Not for ILL. 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 9919157280001571; HELD; Vol. 62, no. 7 (1984) - v. 74 (1996)[Impf.]. 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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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); OS; YOS-SER 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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