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

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10.1002/ffj.3332

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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",

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doi = "10.1002/ffj.3332",

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volume = "31",

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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 - http://www.scopus.com/inward/record.url?scp=84976531347&partnerID=8YFLogxK

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

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