The Reaction of Some Olefin Oxides With the Naphthols

Abstract

In order to add to the existing knowledge of the chemistry of olefin oxides, particularly the factors that govern the direction of ring opening in unsymmetrical oxides, the reactions of several styrene oxides with various phenols have been studied and reported (1-8). The present report describes the reactions of some of these styrene oxides and of cyclohexene oxide with the naphthols, principally with 2-naphthol. The reactions of these styrene oxides with 2-naphthol were found to deviate somewhat from those reported with phenol in that more nuclear attack was observed, probably a result of the greater nucleophilic character of the naphthol nucleus. Cyclohexene oxide was included in this study to ascertain whether it would be similar in behavior to propylene oxide, as might be expected, in contrast to styrene oxide. The postulated importance (1,3,4,6) of a resonancestabilized intermediate in the reactions of the styrene oxides to form primary alcohols is again further supported by these experimental results.1 This paper is based on a portion of the Ph.D. dissertation (1951) of Rudolph Rosenthal.

Synthesis and 1H NMR structural analysis of 11‐aryl/heteroarylnaphtha[2,1‐b]furans: X‐ray crystal structure of 11‐(4′‐pyridyl)naphtho[2,1 ‐b]furan

“…Calcd. for C 17 Compound 10 (0.122 g, 0.5 mmol) was dissoved in dry THF (2 ml) and a few drops of CH 3 I were added. The reaction flask was tightly stoppered and left at room temperature for a week to deposit crystals of 11.…”

“…Though, a number of 11-alkyl/aryl naphtho[2,1-b]furans have been described in the literature [16][17][18][19][20][21][22], surprisingly only limited information is currently available on their spectral properties or molecular structures [23]. To our knowledge, no report dealing with the conformational orientation in C-11 aryl naphtho [2,1-b]furans has appeared to date.…”