INTRAMOLECULAR REACTIVITY OF FUNCTIONALIZED ARYLCARBENES - 1-(HYDROXYMETHYL)-9-FLUORENYLIDENE

Authors
KIRMSE W KRZOSSA B
Citation
W. Kirmse et B. Krzossa, INTRAMOLECULAR REACTIVITY OF FUNCTIONALIZED ARYLCARBENES - 1-(HYDROXYMETHYL)-9-FLUORENYLIDENE, Tetrahedron letters, 39(8), 1998, pp. 799-802
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
8
Year of publication
1998
Pages
799 - 802
Database
ISI
SICI code
0040-4039(1998)39:8<799:IROFA->2.0.ZU;2-M
Abstract
Photolyses of 9-diazo-1-fluorenylmethanol (22) in benzene or MeCN affo rd greater than or equal to 95% of fluorene-1-carbaldehyde (14). In me thanol, 14 and 9-methoxy1-fluorenylmethanol (24) are formed competitiv ely from 22. Intramolecular hydrogen transfer of triplet 1-(hydroxymet hyl)-9-fluorenylidene (12) appears to be the major reaction path leadi ng to 14. The photoenol 13 is suggested as an intermediate. (C) 1998 E lsevier Science Ltd. All rights reserved.