Synthesis and Properties of Substituted 1,6-Dioxapyrene Donors
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Synthesis and Properties of Substituted 1,6-Dioxapyrene Donors. / Christensen, J. B.; Bechgaard, K.; Johannsen, I.
I: Journal of Organic Chemistry, Bind 56, Nr. 25, 01.12.1991, s. 7055-7058.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Synthesis and Properties of Substituted 1,6-Dioxapyrene Donors
AU - Christensen, J. B.
AU - Bechgaard, K.
AU - Johannsen, I.
PY - 1991/12/1
Y1 - 1991/12/1
N2 - The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-l,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.
AB - The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-l,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.
UR - http://www.scopus.com/inward/record.url?scp=0039380734&partnerID=8YFLogxK
U2 - 10.1021/jo00025a020
DO - 10.1021/jo00025a020
M3 - Journal article
AN - SCOPUS:0039380734
VL - 56
SP - 7055
EP - 7058
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 25
ER -
ID: 261047067