dc.contributor.author | Brimble, Margaret | en |
dc.contributor.author | Elliott, RJE | en |
dc.date.accessioned | 2011-09-19T00:16:20Z | en |
dc.date.issued | 1997 | en |
dc.identifier.citation | TETRAHEDRON 53(22):7715-7730 02 Jun 1997 | en |
dc.identifier.issn | 0040-4020 | en |
dc.identifier.uri | http://hdl.handle.net/2292/8051 | en |
dc.description.abstract | Addition of 1-trimethylsilyloxybuta-1,3-diene 2 to the quinones 4,5,6,17,18,19,20 bearing formyl, acetyl, methoxycarbonyl or carboxamide substituents at C-2, afforded the Diels-Alder adducts 11,12,13,25,26,27,28 whereas addition of 2-trimethylsilyloxyfuran 3 afforded the fragmentation products 29,30,31,35,36,37,38. Quinones 7,21 bearing a carboxyl group at C-2 afforded 1,4-naphthoquinone and 9,10-anthracenedione with 2 and no adducts were isolated from reaction with 3. Benzoquinone-sulfide 8 afforded Diels-Alder adduct 14 and fragmentation product 32 with 2 and 3 respectively whereby reaction occurred on the less substituted double bond. No adducts were isolated upon treatment of naphthoquinone-sulfide 22 with either 2 or 3. The Diels-Alder adducts of benzoquinone-sulfoxide 9 and naphthoquinone-sulfoxide 23 with 2 underwent facile aromatisation to 1,4-naphthoquinone and 9,10-anthracenedione with 2. Addition of 3 to 9 afforded fragmentation product 33 whereas analogous reaction with 23 was unsucccessful. Addition of dienes 2,3 to benzoquinone-sulfone 10 afforded fragmentation products 16,34 respectively, whereas naphthoquinone-sulfone 24 afforded 9,10-anthracendione with 2 and no products with 3. | en |
dc.language | EN | en |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | en |
dc.relation.ispartofseries | Tetrahedron | en |
dc.rights | Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0040-4020/ | en |
dc.rights.uri | https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm | en |
dc.subject | DIELS-ALDER ADDUCTS | en |
dc.subject | ACTIVATED QUINONES | en |
dc.subject | KETENE ACETALS | en |
dc.subject | REARRANGEMENT | en |
dc.subject | ANTIBIOTICS | en |
dc.subject | ANNULATION | en |
dc.title | Addition of Silyloxydienes to 2-Substituted 1,4-Benzoquinones and 1,4-Naphthoquinones | en |
dc.type | Journal Article | en |
dc.identifier.doi | 10.1016/S0040-4020(97)00436-5 | en |
pubs.issue | 22 | en |
pubs.begin-page | 7715 | en |
pubs.volume | 53 | en |
dc.rights.holder | Copyright: 1997 Elsevier Ltd. | en |
pubs.end-page | 7730 | en |
dc.rights.accessrights | http://purl.org/eprint/accessRights/RestrictedAccess | en |
pubs.subtype | Article | en |
pubs.elements-id | 33958 | en |
pubs.org-id | Science | en |
pubs.org-id | Chemistry | en |
pubs.org-id | Science Research | en |
pubs.org-id | Maurice Wilkins Centre (2010-2014) | en |
pubs.record-created-at-source-date | 2010-09-01 | en |