In:
Zeitschrift für Naturforschung B, Walter de Gruyter GmbH, Vol. 77, No. 7-8 ( 2022-07-26), p. 531-541
Abstract:
Low temperature reactions of 1,4-dichloro-2,5-dimethoxybenzene with two equivalents of lithium diisopropylamide (LDA) followed by quenches with chlorophosphines ClPR 2 ( R = Ph or i Pr) yielded 1,4-bis(diphenylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene ( 1a ) and 1,4-bis(diisopropylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene ( 1b ). Reactions of 1a-b with 30% hydrogen peroxide yielded 1,4-bis(diphenylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene ( 2a ) and 1,4-bis(diisopropylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene ( 2b ). Subjecting compounds 2a-b to BBr 3 /CH 3 OH resulted in 2,5-bis(diphenylphosphinyl)-3,6-dichlorohydroquinone 3a and 2,5-bis(diisopropylphosphinyl)-3,6-dichlorohydroquinone 3b . Reactions of 3a-b with K 2 S 2 O 8 under basic conditions followed by acidification allowed for isolation of 2,5-bis(diphenylphosphinyl)-3,6-dihydroxy-quinone ( 4a ) and 2,5-bis(diisopropylphosphinyl)-3,6-dihydroxy-quinone ( 4b ). Compounds 1a-b – 4a-b were fully characterized by spectroscopic methods (nuclear magnetic resonance [FT-NMR] spectroscopy, infrared [FT-IR] spectroscopy, and high resolution mass spectrometry [HRMS]); 3a-b and 4a-b were also investigated by cyclic voltammetry. Compounds 1a-b , 2a , and 4a-b were also characterized by single-crystal X-ray diffraction methods.
Type of Medium:
Online Resource
ISSN:
0932-0776
,
1865-7117
DOI:
10.1515/znb-2022-0021
Language:
English
Publisher:
Walter de Gruyter GmbH
Publication Date:
2022
detail.hit.zdb_id:
2078109-X
detail.hit.zdb_id:
124635-5
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