Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas

Michael B. McGinnis, Kurt Vagle, James F. Green, Lay Choo Tan, Ronald Palmer, John Siler, Richard M. Pagni, George Kabalka

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A series of boronated aluminas was prepared by the reaction of BX3 (X = F, Cl, Br) with alumina or by a two-step synthesis involving the reaction of BH3·Me2S with alumina and then with I2. The modified aluminas, BXn/AL2O3, were found to have n = 3 (F), n = 1.5 (Cl), n = 1 (Br), and n = 1 (I). The acidity of the solids (indicator dyes) was large and decreased in the order I ∼ Br > Cl > F. The solids catalyzed the Diels-Alder reactions of methyl acrylate with cyclopentadiene and isoprene with methyl acrylate, both of which occurred in high yield and with high selectivity. The regioselectivity of the isoprene/methyl acrylate reaction in fact is higher than seen previously. The results of the heterogeneous reactions were compared to those catayzed by B-bromo- and B-chlorocatecholborane, which serve as models for the boronated aluminas.

Original languageEnglish (US)
Pages (from-to)3496-3500
Number of pages5
JournalJournal of Organic Chemistry
Volume61
Issue number10
DOIs
StatePublished - May 17 1996
Externally publishedYes

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Aluminum Oxide
Cyclopentanes
Regioselectivity
Acidity
Coloring Agents
methyl acrylate
isoprene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas. / McGinnis, Michael B.; Vagle, Kurt; Green, James F.; Tan, Lay Choo; Palmer, Ronald; Siler, John; Pagni, Richard M.; Kabalka, George.

In: Journal of Organic Chemistry, Vol. 61, No. 10, 17.05.1996, p. 3496-3500.

Research output: Contribution to journalArticle

McGinnis, MB, Vagle, K, Green, JF, Tan, LC, Palmer, R, Siler, J, Pagni, RM & Kabalka, G 1996, 'Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas', Journal of Organic Chemistry, vol. 61, no. 10, pp. 3496-3500. https://doi.org/10.1021/jo951077m
McGinnis MB, Vagle K, Green JF, Tan LC, Palmer R, Siler J et al. Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas. Journal of Organic Chemistry. 1996 May 17;61(10):3496-3500. https://doi.org/10.1021/jo951077m
McGinnis, Michael B. ; Vagle, Kurt ; Green, James F. ; Tan, Lay Choo ; Palmer, Ronald ; Siler, John ; Pagni, Richard M. ; Kabalka, George. / Selectivities of Diels-Alder reactions catalyzed by highly acidic boronated aluminas. In: Journal of Organic Chemistry. 1996 ; Vol. 61, No. 10. pp. 3496-3500.
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AU - Green, James F.

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AU - Palmer, Ronald

AU - Siler, John

AU - Pagni, Richard M.

AU - Kabalka, George

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