Student or educator? Sign up with your school email and get 6 months of Pro free.
CoChat
Sign Up
Cited by 311

The DOI matches its Crossref record.

A Scalable Synthesis of Meso-Substituted Dipyrromethanes

Laha, Joydev K., Dhanalekshmi, Savithri, Taniguchi, Masahiko, Ambroise, Arounaguiry, Lindsey, Jonathan S.·2003·Organic Process Research & Development
DOI 10.1021/op034083q
Open this paper in CoChat — free account

Abstract

A one-flask synthesis of meso-substituted dipyrromethanes has been refined. The procedure entails reaction of an aldehyde in 100 equiv of pyrrole as the solvent containing a mild Lewis acid (e.g., InCl 3 ) at room temperature. Following removal and recovery of excess pyrrole, the dipyrromethane is obtained by crystallization. The procedure generates minimal waste and does not require aqueous/organic extraction, chromatography, or distillation. The procedure has been scaled linearly to obtain >100 g of 5-phenyldipyrromethane. The utility of various analytical methods for characterizing dipyrromethanes has been investigated.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/op034083q

Cites

Statistics

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

No references could be resolved yet.

Research works printed but not linked: 55

  1. Treibs A., 1968, Liebigs Ann. Chem., 718, 183, 10.1002/jlac.19687180118 · doi:10.1002/jlac.19687180118
  2. Chong R., 1969, Aust. J. Chem., 22, 229, 10.1071/CH9690229 · doi:10.1071/ch9690229
  3. Clezy P. S., 1969, Aust. J. Chem., 22, 239, 10.1071/CH9690239 · doi:10.1071/ch9690239
  4. Wilson R. M., 1987, J. Org. Chem., 52, 2699, 10.1021/jo00389a013 · doi:10.1021/jo00389a013
  5. Wallace D. M., 1993, J. Org. Chem., 58, 7245, 10.1021/jo00077a056 · doi:10.1021/jo00077a056
  6. Setsune J., 1994, J. Chem. Soc., Chem. Commun., 657, 10.1039/c39940000657 · doi:10.1039/c39940000657
  7. Setsune J., 1998, Tetrahedron, 54, 1407, 10.1016/S0040-4020(97)10386-6 · doi:10.1016/s0040-4020(97)10386-6
  8. Volz H., 1997, Angew. Chem., Int. Ed. Engl., 36, 1442, 10.1002/anie.199714421 · doi:10.1002/anie.199714421
  9. Lin V. S.-Y., 2002, J. Inorg. Synth., 33, 55
  10. Nagarkatti J. P., 1974, Synthesis, 186, 10.1055/s-1974-23271 · doi:10.1055/s-1974-23271
  11. Hammel D., 1992, Adv. Mater., 4, 737, 10.1002/adma.19920041105 · DOI
  12. Vigmond S. J., 1992, Anal. Chem., 64, 2763, 10.1021/ac00046a019 · doi:10.1021/ac00046a019
  13. Vigmond S. J., 1994, Tetrahedron Lett., 35, 2455, 10.1016/S0040-4039(00)77142-5 · doi:10.1016/s0040-4039(00)77142-5
  14. Casiraghi G., 1994, J. Org. Chem., 59, 1801, 10.1021/jo00086a035 · doi:10.1021/jo00086a035
  15. Cornia M., 1995, J. Org. Chem., 60, 4964, 10.1021/jo00121a003 · doi:10.1021/jo00121a003
  16. Mizutani T., 1994, J. Am. Chem. Soc., 116, 4240, 10.1021/ja00089a013 · doi:10.1021/ja00089a013
  17. Boyle R. W., 1994, Synlett, 939, 10.1055/s-1994-23056 · doi:10.1055/s-1994-23056
  18. Boyle R. W., 1994, Tetrahedron Lett., 35, 5377, 10.1016/S0040-4039(00)73504-0 · doi:10.1016/s0040-4039(00)73504-0
  19. Staab H. A., 1994, Chem. Ber., 127, 223, 10.1002/cber.19941270132 · doi:10.1002/cber.19941270132
  20. Shipps G., 1994, Tetrahedron Lett., 35, 6823, 10.1016/0040-4039(94)85014-3 · doi:10.1016/0040-4039(94)85014-3
  21. (c) Carell, T. Ph.D. Thesis, Ruprecht-Karls-Universität Heidelberg, 1993.
  22. Wijesekera T. P., 1996, Can. J. Chem., 74, 1868, 10.1139/v96-209 · doi:10.1139/v96-209
  23. Nishino N., 1996, J. Org. Chem., 61, 7534, 10.1021/jo9611576 · doi:10.1021/jo9611576
  24. Lee C.-H., 1994, Tetrahedron, 50, 11427, 10.1016/S0040-4020(01)89282-6 · DOI · Paper page
  25. Gryko D., 2000, J. Org. Chem., 65, 2249, 10.1021/jo9918100 · doi:10.1021/jo9918100
  26. Brückner C., 1997, Chem. Commun., 1689, 10.1039/a704510g · DOI
  27. Boyle R. W., 1998, Org. Synth., 76, 287
  28. Brückner C., 1998, J. Porphyrins Phthalocyanines, 2, 455, 10.1002/(SICI)1099-1409(199811/12)2:6<455::AID-JPP67>3.0.CO;2-C · doi:10.1002/(sici)1099-1409(199811/12)2:6<455::aid-jpp67>3.0.co;2-c
  29. Littler B. J., 1999, J. Org. Chem., 64, 1391, 10.1021/jo982015+ · DOI
  30. Brückner C., 1996, Can. J. Chem., 74, 2182, 10.1139/v96-245 · doi:10.1139/v96-245
  31. Geier G. R., 2000, Org. Lett., 2, 1745, 10.1021/ol005917h · doi:10.1021/ol005917h
  32. Geier G. R., 2002, J. Porphyrins Phthalocyanines, 6, 159, 10.1142/S1088424602000208 · doi:10.1142/s1088424602000208
  33. Geier G. R., 2001, J. Porphyrins Phthalocyanines, 5, 810, 10.1002/jpp.387 · doi:10.1002/jpp.387
  34. Speckbacher M., 2003, Inorg. Chem., 42, 4322, 10.1021/ic026206d · DOI
  35. Babu S. A., 2002, Synlett, 531, 10.1055/s-2002-20488 · doi:10.1055/s-2002-20488
  36. Kobayashi S., 2002, Chem. Rev., 102, 2227, 10.1021/cr010289i · DOI · Paper page
  37. Loewe R. S., 2002, J. Mater. Chem., 12, 3438, 10.1039/B205680A · DOI
  38. Yu L., 2003, Inorg. Chem., 42
  39. Naik R., 2003, Tetrahedron, 59, 2207, 10.1016/S0040-4020(03)00245-X · doi:10.1016/s0040-4020(03)00245-x
  40. Sobral A. J. F. N., 2003, Tetrahedron Lett., 44, 3971, 10.1016/S0040-4039(03)00785-8 · DOI
  41. Cho W.-S., 1998, Bull. Korean Chem. Soc., 19, 314
  42. Dubé T., 2000, Organometallics, 19, 3716, 10.1021/om000502l · doi:10.1021/om000502l
  43. Bucher C., 2001, J. Am. Chem. Soc., 123, 2099, 10.1021/ja005842c · doi:10.1021/ja005842c
  44. Arumugam N., 2001, Bull. Korean Chem. Soc., 22, 932
  45. Depraetere S., 2003, Tetrahedron Lett., 44, 345, 10.1016/S0040-4039(02)02521-2 · doi:10.1016/s0040-4039(02)02521-2
  46. Beer P. D., 2003, Dalton Trans., 603, 10.1039/b210099a · doi:10.1039/b210099a
  47. Dmowski W., 2003, Synthesis, 841, 10.1055/s-2003-38683 · doi:10.1055/s-2003-38683
  48. Ka J.-W., 2000, Tetrahedron Lett., 41, 4609, 10.1016/S0040-4039(00)00672-9 · doi:10.1016/s0040-4039(00)00672-9
  49. Li F., 1997, Tetrahedron, 53, 12339, 10.1016/S0040-4020(97)00770-9 · doi:10.1016/s0040-4020(97)00770-9
  50. Hill C. L., 1985, J. Chem. Soc., Chem. Commun., 1228, 10.1039/C39850001228 · doi:10.1039/c39850001228
  51. Lindsey J. S., 1989, J. Org. Chem., 54, 828, 10.1021/jo00265a021 · DOI
  52. Barrett A. G. M., 1999, J. Chem. Soc., Perkin Trans. 1, 873, 10.1039/a809919g · doi:10.1039/a809919g
  53. Brückner C., 1997, Inorg. Chim. Acta, 263, 279, 10.1016/S0020-1693(97)05700-9 · doi:10.1016/s0020-1693(97)05700-9
  54. Wagenknecht H.-A., 1998, Helv. Chim. Acta, 81, 1506, 10.1002/hlca.19980810554 · doi:10.1002/hlca.19980810554
  55. Wang Q. M., 1995, Synlett, 1267, 10.1055/s-1995-5244 · doi:10.1055/s-1995-5244

Cited by

See all 311

Metadata

Authors
Laha, J. K., Dhanalekshmi, S., Taniguchi, M., Ambroise, A., & Lindsey, J. S.
Venue
Organic Process Research & Development
Publisher
American Chemical Society (ACS)
Published
2003-09-09
Volume
7
Issue
6
Pages
799-812
ISSN
  • 1083-6160 (ISSN-L)
  • 1520-586X
DOI
10.1021/op034083q
OpenAlex
W1976397055
Cited by
311
References
0
FWCI
3.60
Type
journal article
Language
en
Open access
closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

How to cite

Cite CoChat for the checks on this page, and the paper for its own findings.

This page
CoChat. (2026). Citation check: A Scalable Synthesis of Meso-Substituted Dipyrromethanes. https://app.cochat.ai/papers/10.1021/op034083q
The paper
Laha, J. K., Dhanalekshmi, S., Taniguchi, M., Ambroise, A., & Lindsey, J. S. (2003). A Scalable Synthesis of Meso-Substituted Dipyrromethanes. Organic Process Research & Development. https://doi.org/10.1021/op034083q

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.