INTRAMOLECULAR REACTIVITY OF ARYLCARBENES - 2-(ALKOXYMETHYL)PHENYLCARBENES

Authors
KIRMSE W SCHNITZLER D
Citation
W. Kirmse et D. Schnitzler, INTRAMOLECULAR REACTIVITY OF ARYLCARBENES - 2-(ALKOXYMETHYL)PHENYLCARBENES, Tetrahedron letters, 35(11), 1994, pp. 1699-1702
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
11
Year of publication
1994
Pages
1699 - 1702
Database
ISI
SICI code
0040-4039(1994)35:11<1699:IROA-2>2.0.ZU;2-I
Abstract
Both singlet and triplet states contribute to the intramolecular C-H i nsertion reactions of 2(alkoxymethyl)phenylcarbenes, leading to dihydr o-1 H-2-benzopyrans. Competitively, oxygen ylides are generated which eventually give rise to benzocyclobutenes and dihydroisobenzofurans. T he radical pair mechanism of the Stevens rearrangement is confirmed by variation of the alkyl groups and by means of chiral substrates.