372967-83-4

Basic information

• Product Name: 1,2,3,4-tetrahydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1-naphthalenol
• Synonyms: 1,2,3,4-tetrahydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1-naphthalenol
• CAS NO: 372967-83-4
• Molecular Weight: 376.498
• Mol File: 372967-83-4.mol

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetrahydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1-naphthalenol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrahydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1-naphthalenol(372967-83-4)
• EPA Substance Registry System: 1,2,3,4-tetrahydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1-naphthalenol(372967-83-4)

Safety Data

• Hazardous Substances Data: 372967-83-4(Hazardous Substances Data)

Upstream product

• 2977-45-9 2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one 
• 143192-60-3 2-(phenylethynyl)phenylacetylene 

Downstream Products

• 372967-91-4 2,2-dimethyl-1-(2-phenylethynyl-phenylethynyl)-1,2,3,4-tetrahydro-naphthalene 

Relevant articles and documents

Biradicals from benzoenyne-allenes. Application in the synthesis of 11H-benzo[b]fluoren-11-ols, 1H-cyclobut[a]indenes, and related compounds

New synthetic pathways to 11H-benzo[b]fluoren-11-ols, 1H-cyclobut[a]indenes, and related compounds via biradicals generated from benzoenyne-allenes were developed. Treatment of the diacetylenic propargylic alcohols 13, derived from condensation between benzophenones and the lithium acetylide of 1-(2-ethynylphenyl)-2-phenylethyne, with thionyl chloride produced the 11-chloro- 11H-benzo[b]fluorene 14 and, after hydrolysis, the corresponding 11H-benzo[b]fluoren-11-ols 15. The transformation involved a sequence of reactions, including a biradical-forming C2-C6 cyclization (Schmittel cyclization) reaction of the chlorinated benzoenyne-allene intermediates followed by an intramolecular radical-radical coupling to form the formal Diels-Alder adducts. Interestingly, in the case of the diacetylenic propargylic alcohol 26, obtained from dibenzosuberenone (25), an intramolecular [2+2] cycloaddition reaction of the chlorinated benzoenyne-allene intermediate occurred, furnishing the 1H-cyclobut[a]indene 27 exclusively. The dramatic change of the reaction pathway could be attributed to the emergence of a steric strain due to the nonbonded interactions with the chloro substituent along the pathway toward the formal Diels-Alder adduct 31. On the other hand, the non-chlorinated benzoenyne-allene, derived from prototropic isomerization of the diacetylenic hydrocarbon 60, underwent a formal Diels-Alder reaction to furnish the 11H-benzo[b]fluorene-type hydrocarbon 61 exclusively.

Polycyclic Aromatic Compounds via Radical Cyclizations of Benzannulated Enyne-Allenes Derived from Ireland-Claisen Rearrangement

A new synthetic sequence involving the use of Ireland-Claisen rearrangement of propargylic acetates to form the corresponding benzannulated enyne-allenes followed by Schmittel cyclization to generate benzofulvene biradicals for radical cyclizations leadin