94064-42-3

Basic information

• Product Name: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]octylidenehydrazide
• CAS NO: 94064-42-3
• Molecular Formula: C15H20N2O2S
• Molecular Weight: 292.402
• Mol File: 94064-42-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]octylidenehydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]octylidenehydrazide(94064-42-3)
• EPA Substance Registry System: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]octylidenehydrazide(94064-42-3)

Safety Data

• Hazardous Substances Data: 94064-42-3(Hazardous Substances Data)

Upstream product

• 68908-13-4 bicyclo[2.2.2]oct-5-en-2-one 
• 1165952-91-9 cyclohexa-1,3-diene 
• 68069-67-0 (1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one 
• 2716-23-6 bicyclo[2.2.2]octan-2-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 931-64-6 norbornene 

Relevant articles and documents

Thermal chemistry of bicyclo[4.2.0]oct-2-enes

At 300 °C, bicyclo[4.2.0]oct-2-ene (1) isomerizes to bicyclo[2.2.2]oct-2-ene (2) via a formal [1,3] sigmatropic carbon migration. Deuterium labels at C7 and C8 were employed to probe for two-centered stereomutation resulting from C1-C6 cleavage and for one-centered Stereomutation resulting from C1-C8 cleavage, respectively. In addition, deuterium labeling allowed for the elucidation of the stereochemical preference of the [1,3] migration of 1 to 2. The two possible [1,3] carbon shift outcomes reflect a slight preference for migration with inversion rather than retention of stereochemistry; the si/sr product ratio is ～1.4. One-centered stereomutation is the dominant process in the thermal manifold of 1, with lesser amounts of fragmentation and [1,3] carbon migration processes being observed. All of these observations are consistent with a long-lived, conformationally promiscuous diradical intermediate.