ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Cyclofunctionalization of 2-Allyl-phenols with Sulfur Chlorides. Synthesis of 2,3-Dihydrobenzofurfuryl Thioethers by the Reaction of 2-Allyl-phenols with Aromatic Sulfenyl ChloridesReactions of different substituted 2-allyl-phenols (2a-h) with either phenylsulfeny chloride (3) or 4-methyl phenylsulfenyl chloride (4) yield the products of a cyclofunctionali zation 2-phenylthiomethyl 2,3-dihydrobenzofuranes (6a-h) or 2-(4′-methylphenyl) 2,3-dihydrobenzofurane (7a-g), respectively. The identification of the products was carried out by mass spectroscopy and 1H-n.m.r.-spectroscopy. Isomeric compounds, i.e. 3-phenylthio 2,3-dihydrobenzopyranes (10) were not obtained. The reaction is Markovnilov-directed. In the case of the treatment of 2-allyl-phenols with 2-nitro phenylsulfenyl chloride (5) we have obtained mixtures of 2-(2′-nitrophenyl) thiomethyl 2,3-dihydrobenzofuranes (8a-d) and of simple Markovnikov adducts, so-called β-chlorothioethers. The mixtures were identified by 1H-n.m.r.- and mass spectroscopic (9a-d) methods.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19853270212
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