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Volumn 12, Issue 3, 2001, Pages 346-353

The Reaction of Safrole Derivatives with Aluminum Chloride: Improved Procedures for the Preparation of Catechols or their mono-O-Methylated Derivatives and a Mechanistic Interpretation

Author keywords

1,3 benzodioxole; Aluminum chloride; MNDO; Molecular orbitals; Safrole

Indexed keywords


EID: 0035610506     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/s0103-50532001000300005     Document Type: Article
Times cited : (6)

References (80)
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    • (a) 4c (99% yield from 4b): ref. (6c);
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    • (d) 4g (79% overall yield form 4a): Amorim, M. B.; Costa, P. R. R. Braz. Ped. PI BR 86 93629 [Chem. Abstr. 1988, 109, 230527] and Gal, G.; Sletzinger, M.; Pines, S. H. British Patent Appl. 2059955 [Chem. Abstr. 1981, 95, 150202];
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    • (d) 4g (79% overall yield form 4a): Amorim, M. B.; Costa, P. R. R. Braz. Ped. PI BR 86 93629 [Chem. Abstr. 1988, 109, 230527] and Gal, G.; Sletzinger, M.; Pines, S. H. British Patent Appl. 2059955 [Chem. Abstr. 1981, 95, 150202];
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    • 1H NMR duplicated signals at δ 6.06 and 6.07
    • 1H NMR duplicated signals at δ 6.06 and 6.07;
  • 33
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    • 4f was the only non-phenolic product observed (by tic analysis) when the reaction of 4g was interrupted before completeness
    • (b) 4f was the only non-phenolic product observed (by tic analysis) when the reaction of 4g was interrupted before completeness.
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    • note
    • 19. Henceforth, the structures 9b, 9c, 9d, and 10e could be assigned to the chloro ether intermediates obtained from, 4b, 4c, 4d, and 4e, respectively.
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    • ref. 4 and references cited therein
    • (c) ref. 4 and references cited therein.
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    • note
    • -1) than 16c. The energetic, as well as the corresponding structural, data of these complexes are available as supplementary material.
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    • 2) has an extremely low basicity, lower than common ethers. However, the calculated complex 22 shows no significant, and regioselective, changes in the acetalic C-O bond lengths, as observed in complexes 18 to 21. (Formula Presented)
    • (1978) Chem. Rev. , vol.78 , pp. 1
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.