In:
European Journal of Organic Chemistry, Wiley, Vol. 2017, No. 43 ( 2017-11-24), p. 6390-6400
Abstract:
A general method for the construction of diphenyl‐substituted carotenoids has been developed through the stereoselective synthesis of dienyl sulfones with a phenyl substituent. Systematic synthetic pathways to the dienyl sulfones were delineated starting from readily available acetophenones with para ‐substituent X of various electronic natures, which provided the carotenoids with diverse physicochemical characteristics. The sulfone olefination method together with the Ramberg–Bäcklund reaction produced a 9,9′‐ cis ‐10,10′‐diphenylcarotene and all‐ trans ‐9,9′‐diphenylcarotenes. Conductance measurements of the all‐ trans carotenoids by the scanning tunnelling microscopy break‐junction method revealed a positional effect of the phenyl groups as well as a polar effect of the phenyl substituent X according to the electronic nature.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2017.43
DOI:
10.1002/ejoc.201701229
Language:
English
Publisher:
Wiley
Publication Date:
2017
detail.hit.zdb_id:
1475010-7