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17.4.2 Product Subclass 2: Benzoxepins

DOI: 10.1055/sos-SD-017-00991

von Angerer, S.Science of Synthesis, (200417653.

General Introduction

While the monocyclic oxepins are of considerable theoretical interest, their benzo analogues have practical importance because some show pharmacological activity. The first example of this type of compound, a dibenzoxepin, was obtained in 1911 by the degradation of morphothebaine.[‌1‌] Three different monobenzoxepins are possible, these are named simply by locating the position of the oxygen atom; i.e. 1-benzoxepin (1), 2-benzoxepin (2), 3-benzoxepin (3) (it should be noted that 2-benzoxepin has an unfavorable o-quinonoid structure). Among the four possible dibenzoxepins 47 dibenz[b,d]oxepin (4) and dibenz[b,f]oxepin (6) are stable compounds, but the others, like 2-benzoxepin, are o-quinonoid in type and have only theoretical interest. Benzoannulation across all of the double bonds leads to tribenz[b,d,f]oxepin (8) (Scheme 1).

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Meeeee 8 Meeeeeee ee Meeee eeee eee Meeeeeeeeeee Meeeeeeee[‌88‌‌88‌]

Meeeeee eeeeeee ee eeeeeeeeeee eee eeee. Mee 8-eeeeeeeeeee eeeeee (88) eee eeeeeeee (88) eee ee eeeeeeee eeee Meeeeeeeeee eeeeeee (Meeeee 8),[‌88‌] eee eee eee eeeeeeeeee 8-eeeeeeeeeee, eeeeeeeeee (88) eee eeeeeeeeeeeeeeeee, eeee eeeeeeeeee ee e eeeeeeee-eeeeee eeeeeeeeeeeee ee ee eeeeeee ee Meeeeee eeeeeeeeee eee. Meeee. Meee eeeeeeeeee eee eeeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeeee-8.[‌88‌] Meeeeee eeeee-eeeeeeeee eeeeeeeeee ee eeeeeeeeee eeee (88), eeeee ee eeeeeee eeeeeee ee eeeeeeeee (88).[‌88‌] Meeee eeeee e 8-eeeeeeeeeeeeeee-8,8-eeeeeee-8-eeeeeeeeee eeeeeeeee eee eeee eeeeeee eeeeeeeeeee eeeeeeeeee eeeeeeee.[‌88‌] Mee ee eee eeeeeeeeeeee ee eee eeeeeeeee ee eee eeee Meeeeeee eeeeeeee Meee. ee eee eeeeee[e,e]eeeeee eeeeeeee (88).[‌88‌,‌88‌] Meeeeee eeeeeee ee e eeeeeee eeeeee[e,e]eeeeee ee eeeeeeeeeeeeee eeee (88), eeeee eee ee eeeeeeee eeee Meeeee eeeeeeeee.[‌88‌] Mee eeeeeeee-eeee eeeeeeeee ee Meeeeeeeeeee eeeeee eee e eeeee ee 8-eeeeeeeeeeeeeeeeeee eeee eeeeeee ee eeeee eeeeeee eeeeeee M8 ee eee eeeeeeeeeeee eeee eee M8 ee eee 8-eeeeee eeeeeeeeeee, eeee eeeeeee e ­eeeee-eeeee 8,8-eeeeeeeeeeeee eeeeeeeee.[‌88‌‌88‌] Me eeee (ee ee eeeee) eeeee eeeeeeeee eeeeeee e Meeeeee-eeee eeeeeeeeeee eeee eeeee eee eeeeeeee eeeeeeeeeee ee eeeeee eeeeee[e,e]eeeeeee, eeee ee eeeeeeeeeeee (88) eee eeeeeeeeeeee (88).[‌88‌,‌88‌] Mee eeee eeeee eeeeeeeee ee eee eeeeee eee eeeeeee eeeeeeee ee eeee eeeee ee eeeeeeeeeeeeee eeeeeeeee, eeee ee eeeeeeeeeeeeee (88) (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeee Meeeeeee eeee Meeeeeeeee ee Meeeeeeeeeee Meeeeeeeee[‌88‌‌88‌]

References


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