메뉴 건너뛰기




Volumn , Issue 14, 2009, Pages 2324-2328

A safe, convenient and efficient one-pot synthesis of α-chloroketone acetals directly from ketones using iodobenzene dichloride

Author keywords

Acetals; Dichloride; Halogenation; Hypervalent iodine; Iodobenzene; Ketones

Indexed keywords

ACETALS; AROMATIC KETONES; DICHLORIDE; HYPERVALENT IODINE; IODOBENZENE; ONE-POT SYNTHESIS; ROOM TEMPERATURE;

EID: 67651103010     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216856     Document Type: Article
Times cited : (34)

References (43)
  • 6
    • 0001368578 scopus 로고
    • For sulfuryl chloride as a chlorinating reagent, see
    • (a) For sulfuryl chloride as a chlorinating reagent, see: Wyman, D. P.; Kaufman, P. R. J. Org. Chem. 1964, 29, 1956.
    • (1964) J. Org. Chem , vol.29 , pp. 1956
    • Wyman, D.P.1    Kaufman, P.R.2
  • 7
    • 33947465641 scopus 로고
    • For cupric chloride as a chlorinating reagent, see
    • (b) For cupric chloride as a chlorinating reagent, see: Kochi, J. K. J. Am. Chem. Soc. 1955, 77, 5274.
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 5274
    • Kochi, J.K.1
  • 8
    • 0033583292 scopus 로고    scopus 로고
    • For p-toluenesulfonyl chloride as a chlorinating, see: Brummond, K. M.; Gesenberg, K. D. Tetrahedron Lett. 1999, 40, 2231.
    • (c) For p-toluenesulfonyl chloride as a chlorinating, see: Brummond, K. M.; Gesenberg, K. D. Tetrahedron Lett. 1999, 40, 2231.
  • 9
    • 0001509163 scopus 로고    scopus 로고
    • For N-chlorosuccinimide as a chlorinating reagent, see: Buu-Hoï, N. P.; Demerseman, P. J. Org. Chem. 1953, 18, 649.
    • (d) For N-chlorosuccinimide as a chlorinating reagent, see: Buu-Hoï, N. P.; Demerseman, P. J. Org. Chem. 1953, 18, 649.
  • 38
    • 67651101708 scopus 로고    scopus 로고
    • One referee surmised that molecular chlorine might be the active species in our system and advised us to check this possibility by carrying out the reaction showed in Scheme 3 in the presence of 4 Å MS. Accordingly, 4′-methylacetophenone was treated with 1.1 equivalents of molecular chlorine in ethylene glycol in the presence of 4 Å MS at room temperature. After 20 hours, 48% of starting material was recovered and only 7% of the desired cyclic ketal of α-chloroketone was obtained, together with 2-methyl-2-p-tolyl-1,3-dioxolane, which formed as the major product (40, Apparently, this result is distinct from that observed with our PhICl2/ethylene glycol/4 Å MS system under which the same cyclic ketal of α-chloroketone was obtained in 95% yield within only 30 minutes Table 1, entry 5, Therefore, we believe that the mechanism shown in Scheme 1 is still preferable
    • 2/ethylene glycol/4 Å MS system under which the same cyclic ketal of α-chloroketone was obtained in 95% yield within only 30 minutes (Table 1, entry 5). Therefore, we believe that the mechanism shown in Scheme 1 is still preferable.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.