Structure-odor correlation, XXI. Olfactory properties and convenient synthesis of furans and thiophenes related to rose furan and perillene and their isomers
✍ Scribed by Weyerstahl, Peter ;Schenk, Anja ;Marschall, Helga
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 559 KB
- Volume
- 1995
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Starting from 3‐bromofuran (1) or 3‐bromothiophene (2) via alkylation in 2‐position (→ 3–8) followed by the corresponding second alkylation in 3‐position, we obtained rose furan (9), rose thiophene (10), and their analogs 11–16. From the α,β‐unsaturated esters 17–20 by hydrogenation (→ 21–24), DIBAH reduction (→ 25–28), and Wittig reaction, perillene (29), thioperillene (30), and their analogs 29–36 were obtained. Olfactory evaluation showed that the difference between the furans and thiophene derivatives is remarkably small, particularly for perillene (29) compared with thioperillene (30), and their analogs. Also the influence of position and structure of the side chain is lower than expected within the compared compounds 9–36.