PMID- 25927156
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20150714
LR  - 20150515
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 80
IP  - 10
DP  - 2015 May 15
TI  - Azulenylcarbene and naphthylcarbene isomerizations. Falling solid flash vacuum 
      pyrolysis.
PG  - 5030-4
LID - 10.1021/acs.joc.5b00412 [doi]
AB  - 1-Azulenylcarbene 18 has been generated from 5-(1-azulenyl)tetrazole and the 
      sodium salt of azulene-1-carbaldehyde tosylhydrazone using the falling solid 
      flash vacuum pyrolysis (FS-FVP) method. The principal products, which are also 
      formed from both 1- and 2-naphthylcarbenes, cyclobuta[de]naphthalene 6, 
      cyclopenta[cd]indene 16, and benzofulvenallene 17, are explained in terms of two 
      reaction paths, (a) a rearrangement to benzofulvenyl-7-carbene 13 and (b) a 
      rearrangement to 1-naphthylcarbene 1. Moreover, 16 is also formed from 
      2-azulenylcarbene 30, thereby indicating the occurrence of a 
      2-azulenylcarbene-1-azulenylcarbene rearrangement. The reaction mechanisms are 
      supported by density functional theory calculations at the B3LYP/6-31G** level, 
      which indicate that all the rearrangements have activation barriers of <35 
      kcal/mol, thus making them readily achievable under FVP conditions.
FAU - Kvaskoff, David
AU  - Kvaskoff D
AD  - daggerSchool of Chemistry and Molecular Biosciences, The University of Queensland, 
      Brisbane, Qld 4072, Australia.
FAU - Becker, Jurgen
AU  - Becker J
AD  - double daggerFachbereich Chemie der Philipps-Universitat Marburg, D-35037 Marburg, Germany.
FAU - Wentrup, Curt
AU  - Wentrup C
AD  - daggerSchool of Chemistry and Molecular Biosciences, The University of Queensland, 
      Brisbane, Qld 4072, Australia.
AD  - double daggerFachbereich Chemie der Philipps-Universitat Marburg, D-35037 Marburg, Germany.
LA  - eng
PT  - Journal Article
DEP - 20150507
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
EDAT- 2015/05/01 06:00
MHDA- 2015/05/01 06:01
CRDT- 2015/05/01 06:00
PHST- 2015/05/01 06:00 [entrez]
PHST- 2015/05/01 06:00 [pubmed]
PHST- 2015/05/01 06:01 [medline]
AID - 10.1021/acs.joc.5b00412 [doi]
PST - ppublish
SO  - J Org Chem. 2015 May 15;80(10):5030-4. doi: 10.1021/acs.joc.5b00412. Epub 2015 
      May 7.