The cyclotrimerisation of (+)-camphor

Authors
Fabris, F De Martin, A De Lucchi, O
Citation
F. Fabris et al., The cyclotrimerisation of (+)-camphor, TETRAHEDR L, 40(51), 1999, pp. 9121-9124
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
51
Year of publication
1999
Pages
9121 - 9124
Database
ISI
SICI code
0040-4039(199912)40:51<9121:TCO(>2.0.ZU;2-2
Abstract
Naturally occurring (+)-camphor was converted into 2-bromobornene and metal lated at the 3-position by lithium and trimethyltin. The latter tin derivat ive, treated with Cu(NO3)(2). 3H(2)O in THF affords the syn and anti cyclot rimers plus a number of byproducts. The rather unexpected formation of the anti stereoisomer plus the structure of several byproducts confirm a mechan istic proposal based on a Sn-Sn coupling process. (C) 1999 Elsevier Science Ltd. All rights reserved.