Large PAHs by reductive peri-peri "dimerization" of phenalenones

Sergey Pogodin; Israel Agranat

doi:10.1021/ol9909435

Large PAHs by reductive peri-peri "dimerization" of phenalenones

Sergey Pogodin
, Israel Agranat^*

^*Corresponding author for this work

Institute of Chemistry

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

26 Scopus citations

Abstract

(formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl₄/LiAlH₄/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri "dimerization" of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D_2h-1, the most stable conformation, resembles the Clar picture of 1.

Original language	English
Pages (from-to)	1387-1390
Number of pages	4
Journal	Organic Letters
Volume	1
Issue number	9
DOIs	https://doi.org/10.1021/ol9909435
State	Published - 4 Nov 1999

Access to Document

10.1021/ol9909435

Cite this

@article{a19d7ed66cf549e9957b078940c84780,

title = "Large PAHs by reductive peri-peri {"}dimerization{"} of phenalenones",

abstract = "(formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri {"}dimerization{"} of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D2h-1, the most stable conformation, resembles the Clar picture of 1.",

author = "Sergey Pogodin and Israel Agranat",

year = "1999",

month = nov,

day = "4",

doi = "10.1021/ol9909435",

language = "אנגלית",

volume = "1",

pages = "1387--1390",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Large PAHs by reductive peri-peri "dimerization" of phenalenones

AU - Pogodin, Sergey

AU - Agranat, Israel

PY - 1999/11/4

Y1 - 1999/11/4

N2 - (formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri "dimerization" of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D2h-1, the most stable conformation, resembles the Clar picture of 1.

AB - (formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri "dimerization" of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D2h-1, the most stable conformation, resembles the Clar picture of 1.

UR - https://www.scopus.com/pages/publications/0001755169

U2 - 10.1021/ol9909435

DO - 10.1021/ol9909435

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0001755169

SN - 1523-7060

VL - 1

SP - 1387

EP - 1390

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Large PAHs by reductive peri-peri "dimerization" of phenalenones

Abstract

Access to Document

Other files and links

Fingerprint

Cite this