Solvent effect on the debromination/dehydrobromination of bromo-damascone

Ying Ying Cheng; Tian Lu Ren; Bao Hua Xu; Hai Sheng Tao; Suo Jiang Zhang

doi:10.1002/ffj.3332

Solvent effect on the debromination/dehydrobromination of bromo-damascone

Ying Ying Cheng
, Tian Lu Ren
, Bao Hua Xu^*
, Hai Sheng Tao
, Suo Jiang Zhang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The dehydrogenative synthesis of β-damascenone from β-damascone via the related allyl bromide intermediate was studied in depth. The requisite dehydrobromination thereof was found strongly solvent system dependent. Under respective conditions, the product was identified as dehydrogenation-derived a, 4-alkoxy-derived b and 4-oxo-derived c, accordingly. In addition, the conversion from b to a was successfully accomplished, thereby offering an alternative access (with one step more) to reach β-damascenone.

Original language	English
Pages (from-to)	420-428
Number of pages	9
Journal	Flavour and Fragrance Journal
Volume	31
Issue number	6
DOIs	https://doi.org/10.1002/ffj.3332
Publication status	Published - 1 Nov 2016
Externally published	Yes

Keywords

allyl bromide
dehydrobromination
solvent effect
substitution
β-damascenone

Access to Document

10.1002/ffj.3332

Cite this

@article{dd63ee92d20c4197aa1db9f64bc9a6b8,

title = "Solvent effect on the debromination/dehydrobromination of bromo-damascone",

abstract = "The dehydrogenative synthesis of β-damascenone from β-damascone via the related allyl bromide intermediate was studied in depth. The requisite dehydrobromination thereof was found strongly solvent system dependent. Under respective conditions, the product was identified as dehydrogenation-derived a, 4-alkoxy-derived b and 4-oxo-derived c, accordingly. In addition, the conversion from b to a was successfully accomplished, thereby offering an alternative access (with one step more) to reach β-damascenone.",

keywords = "allyl bromide, dehydrobromination, solvent effect, substitution, β-damascenone",

author = "Cheng, \{Ying Ying\} and Ren, \{Tian Lu\} and Xu, \{Bao Hua\} and Tao, \{Hai Sheng\} and Zhang, \{Suo Jiang\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 John Wiley \& Sons, Ltd.",

year = "2016",

month = nov,

day = "1",

doi = "10.1002/ffj.3332",

language = "English",

volume = "31",

pages = "420--428",

journal = "Flavour and Fragrance Journal",

issn = "0882-5734",

publisher = "John Wiley and Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Solvent effect on the debromination/dehydrobromination of bromo-damascone

AU - Cheng, Ying Ying

AU - Ren, Tian Lu

AU - Xu, Bao Hua

AU - Tao, Hai Sheng

AU - Zhang, Suo Jiang

PY - 2016/11/1

Y1 - 2016/11/1

N2 - The dehydrogenative synthesis of β-damascenone from β-damascone via the related allyl bromide intermediate was studied in depth. The requisite dehydrobromination thereof was found strongly solvent system dependent. Under respective conditions, the product was identified as dehydrogenation-derived a, 4-alkoxy-derived b and 4-oxo-derived c, accordingly. In addition, the conversion from b to a was successfully accomplished, thereby offering an alternative access (with one step more) to reach β-damascenone.

AB - The dehydrogenative synthesis of β-damascenone from β-damascone via the related allyl bromide intermediate was studied in depth. The requisite dehydrobromination thereof was found strongly solvent system dependent. Under respective conditions, the product was identified as dehydrogenation-derived a, 4-alkoxy-derived b and 4-oxo-derived c, accordingly. In addition, the conversion from b to a was successfully accomplished, thereby offering an alternative access (with one step more) to reach β-damascenone.

KW - allyl bromide

KW - dehydrobromination

KW - solvent effect

KW - substitution

KW - β-damascenone

UR - https://www.scopus.com/pages/publications/84976531347

U2 - 10.1002/ffj.3332

DO - 10.1002/ffj.3332

M3 - Article

AN - SCOPUS:84976531347

SN - 0882-5734

VL - 31

SP - 420

EP - 428

JO - Flavour and Fragrance Journal

JF - Flavour and Fragrance Journal

IS - 6

ER -

Solvent effect on the debromination/dehydrobromination of bromo-damascone

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this