Synthesis of poly-substituted phenols from baylis-hillman adducts and 1,3-dinitroalkanes

Bulletin of the Korean Chemical Society

Volumn 29, Issue 3, 2008, Pages 701-704

  Da, Yeon Park ^a   Ka, Young Lee ^a   Gowrisankar, Saravanan ^a   Jae, Nyoung Kim ^a  

^a Chonnam National University   (South Korea)

Author keywords

1,3 Dinucleophiles; Baylis hillman adducts; Nitroalkanes; Phenols

Indexed keywords

EID: 41549166560     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2008.29.3.701     Document Type: Article

References (34)

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33. Nishioka, H.; Ohmori, Y.; Iba, Y.; Tsuda, E.; Harayama, T. Heterocycles 2004, 64, 193. During the evaluation process of this paper, one of the reviewers raised the possibility for the structure of compound 5a as the one having the two substituted groups (hydroxyl and nitro) in the reverse direction. However, we do not have further evidence at this stage, unfortunately.
34. During the workup stage, when we adjusted the pH of the water phase too acidic (pH = 1-2) the yield of 4a was decreased and the yield of 5a was increased slightly. On the contrary, when we poured the reaction mixture in neutral water, we could obtain 4a in similar yield but we could not observe the formation of 5a. Thus, we adjusted the pH of the water phase as 5-6 throughout the whole entries in Table 1. We also examined one-pot reaction of 1a and 2a in DMF in the presence of K2CO3. Similar amount of 5a was observed on TLC but the yield of 4a was decreased much.