Generation and trapping of an unsymmetrical, caged pyramidalized alkene

Authors
Marchand, AP Namboothiri, INN Ganguly, B Watson, WH Bodige, SG
Citation
Ap. Marchand et al., Generation and trapping of an unsymmetrical, caged pyramidalized alkene, TETRAHEDR L, 40(28), 1999, pp. 5105-5109
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
28
Year of publication
1999
Pages
5105 - 5109
Database
ISI
SICI code
0040-4039(19990709)40:28<5105:GATOAU>2.0.ZU;2-I
Abstract
Low-temperature reaction of 2,5-diiodopentacyclo[5.3.0.0(2,5).0(3,9).0(4,8) ]decane(7) with MeLi in dry THF results in elimination of I-2 with concomit ant formation of the corresponding caged alkene, 8. This highly strained py ramidalized alkene is trapped stereoselectively by 1,3-diphenylisobenzofura n(DPIBF) to afford a single [4+2] cycloadduct, 9b. The corresponding reacti on of 8 with 9-methoxyanthracene proceeds with relatively low regioselectiv ity. The origins of these phenomena have been investigated computationally. (C) 1999 Elsevier Science Ltd. All rights reserved.