Abstract
AbstractThe synthesis and olfactory properties of a series of 2‐substituted and 2,3‐annulated 1,4‐dioxepan‐6‐ones is reported. By Williamson etherification with 3‐chloro‐2‐(chloromethyl)prop‐1‐ene (6) and subsequent Katsuki–Sharpless oxidation, 1,4‐dioxepan‐6‐one (8 a) and its 2‐methyl (8 b), 2‐propyl (8 c), 2‐isobutyl (8 d), and 2,2,3,3‐tetramethyl derivative (8 e), as well as four 2,3‐annulated 1,4‐dioxepan‐6‐ones 8 h, 8 i, 8 j, and 8 k were synthesised. By etherification with ethyl diazoacetate and subsequent Dieckmann cyclisation, (5aS,9aS)‐9‐bromo‐ and 9‐iodo‐5a,6,7,9a‐tetrahydro‐2 H‐benzo[b][1,4]dioxepin‐3(4 H)‐one (8 f/g) as well as a 2,3‐annulated derivative 8 m from (+)‐limonene were prepared. 2‐Propyl‐1,4‐dioxepan‐6‐one (8 c) was discovered to have a green floral odour with anisic and cinnamic nuances, which could be rationalised by a superposition analysis. The olfactory properties of the 1,4‐dioxepan‐6‐ones synthesised underline the crucial importance of a benzenoid ring system for marine odorants.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
