The chemistry of small ring compounds. part 18 indirect evidence for 2-cyclopropylidenecyclohexadienone as an intermediate
✍ Scribed by W.J.M. van Tilborg; J.R. van der Vecht; H. Steinberg; Th.J. de Boer
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 170 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
AS part of our interest in cyclopropyl compounds with an exocyclic double bond, we have investigated the quaternary ammonium salt 1, l-(o-hydroxyphenyl)cyclo-propyltrimethylammoniumiodide2 under alkaline conditions, normally favouring Hofmann elimination. Heating of 1 with 3.5 eq. of KOH for 36 hrs in refluxing methanol led to substitution of the trimethylamino group by a methoxy group, and isolation of I-(o-hydroxyphenyl)l-methoxycyclopropane 2 in 73% yield. The IR spectrum of 2 shows bands at 3400 cm -I (OH), 2940, 2900 and 2820 cm-' (OCH?), 1025 cm-' (cyclopropyl). The NMR spectrum displays a multiplet with an AA'BB' pattern at * Part of the thesis of W.J.M. van Tilborg,